Why haven’t Spurs won a trophy since 2008?

Inevitably my twitter feed was full last weekend of posts nostalgically remembering that it was exactly 16 years to the day since we beat Chelsea 2-1 in the (Carling) League Cup Final which of course was our last trophy success. 

As well as provoking first-hand memories of the day and the occasion it naturally became an opportunity to lament our lack of tangible success since then. The most, in a gallows humour way, amusing take was the comment that ‘if Spurs’ trophy drought was a person they could now legally have sex’. 

So why exactly haven’t we won a trophy since 2008? 

Quite simply winning a trophy is bloody hard to do – not only do you need luck on your side but unless you have a squad depth of Chelsea, Liverpool or Man City you also have to prioritise cup ties throughout the season often at the expense of league games. Let’s take the successful 2008 League Cup campaign. 

It started under Martin Jol in Autumn 2007. In round 3 we drew Middlesbrough at home. This was a fixture we tended to do well in and had won the previous three home games against Boro. By Round 4 Jol had left and Juande Ramos was in charge for his first home game – against second-tier Blackpool. Both games ended 2-0. 

Under Ramos’ much maligned tenure we actually enjoyed some enjoyable months between December and the Wembley success in February winning five of six games in December including the 2-0 League Cup QF victory over Manchester City (in their pre-Sheikh Mansour form) which saw us through to a semi-final against Arsenal.

Let’s not take anything away from the semi-final result not least the emphatic 5-1 second leg at White Hart Lane – one of the most electric nights I can remember. We played well in the first leg at The Emirates and deserved more than the 1-1 draw but the way we blew them away at White Hart Lane was incredible. However, it can’t be ignored that Wenger selected a significantly under-strength side for the second leg just as Manchester United (that seasons champions) had when knocked out by Coventry in Round 3. 

The final against Chelsea remains one of the best Spurs performances relative to opposition and the occasion. From the opening whistle it was clear that we were ‘on it’. Chelsea would go on to finish runners up in the Premier League and in the Champions League that season. We hoped that this was vindication of Ramos’ appointment – the ability to punch through the glass ceiling that had appeared to evade Martin Jol and his inability to cement a top 4 place (two successive 5th place finishes) and agonising cup exits to both Arsenal and Chelsea in 2007 when we were well placed to win both. 

With the 2008 League Cup won and a place in the following seasons UEFA Cup secured there was little left to play for in the league. That season’s UEFA Cup campaign terminated in March with an unfortunate defeat to PSV on penalties and so the remainder of the season should have been about enjoying Keane and Berbatov and building momentum to go into 2008/09

What followed in the league was mediocre at best – for anyone who remembers watching Spurs through Spring 2008 it was embodiment of ‘being on the beach’. 

Rather than producing the springboard Summer 2008 was traumatic – both Keane and Berbatov left in acrimonious circumstances – it developed into a dramatic false dawn and eight games into the new league season Spurs sat bottom of the league for the first time since 1988. 

Essentially, winning the 2008 League Cup had failed to make any material difference to Spurs’ fortunes.

That’s not to diminish the visceral joy of winning a cup for both players and particularly for fans. The fact that the footage of 2008 sparked so many happy memories is a reminder that football is for fans and those unbridled moments of joy can last a lifetime. However, from the club’s perspective success in 2008 didn’t allow them to keep their best players let alone act as a catalyst to attract better new players. Neither did it create the winning mentality that supposedly ‘winning the first cup’ provides. 

This is common with the other cup winners from outside the cartel of established forces (Arsenal, Manchester Utd, Liverpool) and the nouveau riche (Chelsea and Manchester City). 

Middlesbrough (League Cup 2004) Portsmouth (FA Cup 2008), Birmingham (League Cup 2011), Swansea (League Cup 2013) and Wigan (FA Cup 2013) were all relegated within five years of their cup successes. 

Since 2008 Spurs have been to three finals – 2009 v Manchester United, 2015 v Chelsea and 2021 v Manchester City. On each of those occasions they have lost narrowly and failed to score in each but on each occasion the winners went onto become League Champions (and in both Manchester clubs’ cases Champions League finalists) that season. 

Spurs have also been to the semi-finals twice – 2019 and 2022 – both against Chelsea; the former saw a penalty shoot-out defeat while the latter was more emphatic. The other 11 knock-outs have come against:

Manchester United (2010 Round 4), Arsenal (2011 and 2015 – R3), Liverpool (2016 R4), West Ham (2013 R5, 2017 R4), Stoke (2011/12 R3), Norwich (2012/13 R4), Colchester (2019/20 R3), Nottingham Forest (2022/23 R4) and Fulham (2023/24 R2). 

In all bar the defeats to Manchester Utd in (09/10) and Fulham (23/24) – the latter a penalty shoot-out – Spurs were juggling midweek games with European commitments. Though not an excuse all managers including Ange have failed to find the correct formula in balancing the need to rotate players with having a sufficiently strong and coherent enough XI on the pitch to win games. 

There have been some very obvious failures – the most embarrassing being the penalty defeat to Colchester. West Ham somehow turned around a 2-goal deficit at Wembley in October 2017 just the week before Spurs beat Real Madrid in the Champions League and perhaps the most frustrating was the 2012 loss at Norwich where Spurs led 1-0 through Bale; this defeat particularly irritates as it was the season that Swansea ended up beating Bradford in the final. 

On the whole successive Spurs teams and managers have not had the strength of squad available to be able to navigate the early rounds of the League Cup while also attempting to maintain Top-4 league form and also progressing in European group stages. 

However, the point should be emphasised that the League Cup since the mid-2000s has been increasingly difficult to win due to the importance placed on them by the best teams and their respective managers. 

The League Cup was much maligned during the 90s and its reputation (it was nicknamed the ‘Worthless Cup’ whilst sponsored by Worthington’s when Spurs won it in 1999 owing to the top clubs’ decision to regularly select reserve and youth team players) arguably has never recovered. 

Between 1996 and 2004 the average end league position of the cup winners was 7.22 – during this period Spurs were successful in 1999 and other winners included Leicester City (twice), Blackburn (at Spurs’ expense!) and Middlesbrough. 

1986-19951996 – 20042005 – 20142015 – 2024
Oxford (18)Aston Villa (4)Chelsea (1)Chelsea (1)
Arsenal (4)Leicester (9)Manchester Utd (2)Manchester C (4)
Nottingham Forest (3)Chelsea (4)Chelsea (2)Manchester Utd (6)
Nottingham Forest (9)Tottenham (11)Tottenham (11)Manchester C (1)
Sheffield Weds (23)Leicester (8)Manchester Utd (1)Manchester C (1)
Manchester Utd (2)Liverpool (3)Manchester Utd (2)Manchester C (2)
Arsenal (10)Blackburn (10)Birmingham (18)Manchester C (1)
Aston Villa (10)Liverpool (5)Liverpool (8)Liverpool (2)
Liverpool (4)Middlesbrough (11)Swansea (9)Manchester Utd (3)
  Manchester C (1)Liverpool (TBC)

In the 10 years before that (1986-1995) the average league position of the winners was 9.2 – though this is exaggerated by Sheffield Wednesday – then in the second division beating Manchester United in 1991. 

From 2005 that began to change. Jose Mourinho’s first trophy was the League Cup when his Chelsea side (that would go on to win the league) beat Liverpool in Cardiff. Apart from Spurs (11th) beating Chelsea in 2008 the subsequent five seasons saw either the champions or runners up lifting the League Cup. Spurs help to skew the numbers as over the 10-year period 2005 – 2014 the average league position of the winners is 5.5 (and further skewed by Birmingham’s shock victory over Arsenal in 2011!) 

The trend has continued into the past 10-year cycle and furthered by Pep Guardiola’s commitment to silverware. The average league position of League Cup winners is now as low as 2.33 (and may be lower should Liverpool go on to win the league). Pep has won in four successive years (in which City were champions on three occasions). Chelsea also won the League Cup and went onto become Champions in 2015. During this period the lowest a League Cup winner has finished in the league was 6th and that Mourinho’s Manchester United in 2017 who also went onto win the Europa League that season. 

The FA Cup is slightly different because in contrast to what you might think the competition hasn’t been dominated by the best couple of teams in recent years or at least that’s what the numbers suggest. 

Between 1986 and 1995 it was a largely open field with Coventry (sorry) and Wimbledon both winning against the odds. Everton (15th) and Manchester Utd in 1990 (13th) both came from outside the top half of the table and even Spurs in 1991 only finished the season 10th

From 1996 – 2004 every winner finished in the top 6 with four incidents of the league champions completing a double. Between 2005 – 2014 the pattern largely repeated but for two outliers in Portsmouth in 2008 (8th) and Wigan in 2013 (18th) winning. 

In the most recent period (2015 – 2023) the average league position of the winner has increased to 5th place though there is rationale behind that which is that the ‘Big X’ has increased from four dominant teams to six (if you include Spurs). Arsenal (8th) in 2020 were the lowest placed winners during this period. 

Reaching an FA Cup Final has also got harder – for the latter three periods the average league position of the runners-up has been 10th or 11th. Since 2015 that has changed to 7th. 

Quite how Spurs have failed to reach a final since 1991 remains something of a quirk considering their relative standing in the top division. This blog post from 2021 examined their fate in this competition.

By Eeyore Spurs

Chasing Leeds

Steff, Milo, and Ram dive into the annual TGIAG AGM, the total chaos of our 4-3 win over Leeds, selfies with Deki, and a night out in Nottingham – cobs and all. We’ll also discuss who might need this upcoming break the most? Answers in a Mastodon post, and if you don’t know how to, Milo has the answers. Needs are as needs Musk eh?!!!

A Cannon Of Excuses

This week, Steff, Milo and Aamar (formerly known as Luton and the key founder of this pod) convene to discuss the North London Derby only to find a variety of reasons lie behind its postponement. We will also be looking back at our League Cup semi-final second leg against Chelsea AND having a Conte-perspective natter about our reported transfer targets. Well, put it this way, IF Conte ‘nattered’ we try to frame how he’d feel about such rumoured incomings. All that AND we tell you the two ingredients for a party to be legitimate; they’re so obvious, a 4 year old knows…

Hey Jude

This week, Steff, Gareth, Milo and Ricky look back at the FA Cup 3rd round game against Morecambe and the League Cup Semi Final 1st Leg against Chelsea. We also give an honest evaluation as to who furthered or hindered their cause with Conte. No rants, but honest conversation about some obvious candidates and former fan favourites. 3-2-1 download!

Just A (90) Minute

In this first pod of 2022, Steff, Milo, Ram and Jay look to vary things up as they review the various matches which took place over the festive season, drawing the line at repetition and allowing no prevarication when looking back at Watford, Southampton, Crystal Palace and West Ham. Milo was vary happy to play Stockley Park, his accuracy proving variable, albeit he was dealing with minute details…just tune in. It will make sense.

It’s A Fair Klopp Guv

This week, Milo, Steff and Gareth discuss the return to standards and expectations at Spurs in the wake of the Liverpool match, plus we try to figure out whether football should stay or go during the Covid spike. We also pay light homage to the UEFA Control, Ethics and Disciplinary Body, at the same time covering our tragic exit from the Europa Conference League.

Back To The Future

This week’s pod allows you to go back in time to a match when we had a lovely man swimming out of his depth with a school of his own fish seemingly unwilling to lift a fin or exert a gil (not Bryan!) for club or him. Listen back to our reflections of this dark river moment, knowing that in the end he was rescued and his old school fed a Michelin star diet!!!! Basically, tis a look back at Nuno’s last game sort of in charge against Man U. Listen in and see if we called it the way you saw it…

Jimmy Greaves, Chelsea and Nuno’s Perfect 11

This week, Steff, Ricky and Milo take a moment to reflect on one of the greatest strikers ever, Jimmy Greaves. Try to make sense to make sense of why the injury and travel curse seems to be enjoying THFC so much, work out what is going on inside Nuno’s head and how he might want to play going forward this season. If you want a ‘knees-up-Geezer-slagfest’ don’t bother sticking around! We will also pay tribute to using trash and eating veggie pies. Oh, and someone tries a French Nuno accent to great effect…always look on the bright side of life!

Why can’t we get over the line?

Gareth looks at how we consistently fail to take the final step

Another final comes and goes and the opportunity to end a now 13 year wait for a ‘trophy’ is extended much to the glee of our adversaries.

Let’s park the debate about the significance of trophies (compared to sustained top 4 league finishes) for the moment and just take it as given that winning an FA Cup or League Cup is better than not winning one but that attainment in the League is not a mutually exclusive pursuit. The subject was expertly covered on this week’s the Game is About Glory podcast (from 31:00 specifically).

As was pointed out the cup trophies in England have been hoovered up by those with significantly greater wealth and resource than we have.

YearFA Cup WinnersLeague Cup Winners
2021Chelsea or LeicesterManchester City
2020ArsenalManchester City
2019Manchester CityManchester City
2018ChelseaManchester City
2017ArsenalManchester United
2016Manchester UnitedManchester City
2014ArsenalManchester City
2011Manchester CityBirmingham City
2010ChelseaManchester United
2009ChelseaManchester United
Table 1: Domestic Cup Winners since 2008

The outliers in that list are Wigan, Swansea and Birmingham – it is frustrating that we weren’t able to capitalise on the power vacuum that existed in the competitions in those particular seasons. (but look out for a future blog exploring our bizarre disconnect from the FA Cup). Annoyingly, unlike the mid to late 90’s when The League Cup was legitimately labelled a ‘Mickey Mouse’ trophy as the best teams – Manchester Utd and Arsenal – were apathetic towards it, the big boys now take great pride in winning it – the City players and staff celebrated this fourth successive victory – in a week in which they play a Champions League Semi Final – as if it was their first trophy.

You’ll need little reminding that our last silverware came in 2008…far too long ago but not quite as far back as the meme’s you’ll undoubtedly have been receiving today from West Ham fans whose last trophy arrived when there were only 3 terrestrial TV stations available.

They say you need to lose a final to know how to win one; presumably the heartache of seeing your opponent lift the trophy and celebrate in front of you provides that added determination to get it right next time. Yesterday’s defeat to a vastly superior Manchester City was our fourth successive final defeat dating back to the 2008 League Cup victory over Chelsea.

To lose 4 successive finals is something of an anomaly and coupled with our infamous streak of losing 8 successive FA Cup Semi Final’s suggests that there may be some sort of mental block. Other teams have suffered similarly – Liverpool lost 4 successive finals between 2012 and 2018: FA Cup (2012 v Chelsea) League Cup 2016 (v Manchester City) Europa League 2016 (v Seville) and Champions League (2018 v Real Madrid). Equally Sunderland had gone 8 Wembley appearances without a win between winning the FA Cup in 1973 and beating Tranmere in the Papa Johns Trophy against Tranmere in March this year.

We have been unfortunate that our four finals have all come against undisputedly brilliant teams.

  • 2009 League Cup Final v Manchester Utd (0-0 – lost 4-1 on penalties) – Man Utd were English and European champions and would go on to win the league and reach the Champions League Final.
  • 2015 League Cup Final v Chelsea (0-2) – Chelsea would become Premier League Champions
  • 2019 Champions League Final v Liverpool (0-2) – Liverpool had just recorded 97 PL points; had played in last season’s Champions League Final and would go on to win the league at a canter the following season.
  • 2021 League Cup Final v Man City (0-1) Champions elect and possible Champions League Winners too

I find it hard to accept that Spurs can ‘never win the big games’ because we have done in both the Premier League and Champions League. This hasn’t always been the case between the 90’s and until the early 2010’s our records against Arsenal (no wins between 1999 and 2008), Chelsea (no league wins between 1990 and 2006), Manchester Utd (no win at Old Trafford between 1989 until 2012) were appalling.

However, the league by its format provides few high stakes matches with the instant jeopardy that cup ties provide. The 2010 game at Manchester City is perhaps the closest we have been to a true league ‘cup final’ and of course we won on that memorable evening. Between 2015 and 2018 in the peak Poch era we won fixtures against Manchester City, Man Utd, Liverpool and even finally ended the hoodoo at Stamford Bridge in April 2018 – a result that effectively secured a finish above them.

The last two league campaigns have seen a steady regression back to pre Poch times. In fact, the biggest problem Pochettino created was the rise in expectations. The graphic below shows how between 2010 and 2016 the number of points remained roughly the same (between 62-72) but the incredible 2016/17 (the last at WHL) saw a big fluctuation and sadly since then the points have dropped off at an alarming rate though should consolidate this season probably rising a little.

Figure A: League points gained by Tottenham Hotspur per season since ENIC bough club in 2001

You must also look at the Champions League…though the wins over Inter Milan in the ‘taxi for Macon game’ and the thrilling victory over Real Madrid at Wembley were in the group stages. However, beating Dortmund over two legs in 2019 was an emphatic example of getting the job done. The incredible QF victory over Man City did of come courtesy of a large slice of luck but only by winning the home leg 1-0 and denying City an away goal and then scoring twice in 10 minutes in the return leg provided us a platform whereby we earned the luck needed by a narrow VAR Offside call.

In fact, almost the whole of the group stages in 2019 had aspects of jeopardy – we were going out for more than we were going through and crucial late goals against PSV, Inter and Barcelona saw us progress.

However, when thinking about our inability to win a cup competition, you can’t help think that there may be something intangible missing from the psyche of the club:

2008/09League Cup SFBurnleyWon (2 legs)
2008/09League Cup finalManchester UnitedLost (penalties)
2009/10FA Cup SFPortsmouthLost (0 – 2)
2011/12FA Cup SFChelseaLost (1 – 5)
2014/15League Cup SFSheffield UnitedWon (2 legs)
2014/15League Cup finalChelseaLost (0 – 2)
2016/17FA Cup SFChelseaLost (2 – 4)
2017/18FA Cup SFManchester UnitedLost (1 – 2)
2018/19League Cup SFChelseaLost (2 legs)
2018/19Champions League SFAjaxWon (2 legs)
2018/19Champions League finalLiverpoolLost (0 – 2)
2020/21League Cup SFBrentford Won (2 – 0)
2020/21League Cup finalManchester CityLost (0 – 1)
Table 2: List of all Tottenham Hotspur Cup Semi-Final and Final Appearances since 2008

Once you remove the 3 League Cup Semi-finals against lower league opponents (Burnley, Sheffield Utd and Brentford) it makes the Ajax win very much the outlier in the list. These results have spanned 4 very different managers with some of our best players in a generation all involved.

On further analysis of the 9 defeats seven have occurred against an opponent who we had either already beaten in the league that season and/or finished above in the league too – i.e., we were more than capable of beating them. To have failed on nine successive occasions is surely not just unfortunate even though there is mitigation with nearly all of those games in isolation.

I think we all acknowledge that we are the Junior Partner in the ‘Top 6 cartel’ even though we have enjoyed finishing above all of them at least once in the last 5 seasons. Though a look at their comparative cup result data highlights the bizarre rate of failure that we have experienced.

Figure B: THFC record in Semi-Finals and Finals compared to the other ‘Big 6’ clubs

Our record is undisputedly the worst – especially as the few green bars have invariably come against lower division opposition (LD). Arsenal and Manchester City have the best records (10 – 3) whereas Chelsea have beaten us three times in their record of 9-4. Manchester Utd will need to find a way to reverse any psychological damage suffered in losing their last five significant cup ties.

It is interesting to compare Arsenal with Liverpool. The former has established themselves as Cup Specialists having previously focused on sustained entry to the Champions League. This run started though with highly fortuitous semi final draws in 2014 and 2015 (Wigan and Reading) and then by playing Hull City and Aston Villa in the respective finals. Liverpool, meanwhile, have done the opposite – Klopp has sacrificed domestic cup competitions to prioritise the Champions League as a process towards winning the League but of course with the exception of ‘Dr Tottenham’s help they have lost their last 4 finals having been masters of winning them in the decade prior (they had won 7 of their 8 previous cup finals).

Have we always been this bad in key cup ties? No is the short answer. The 13 semi-finals and finals prior to 2009 which culminated in the 2008 League Cup success are detailed below:

1990/91FA Cup finalNottingham ForestWon
1991/92League Cup SFNottingham ForestLost
1992/93FA Cup SFArsenalLost
1994/95FA Cup SFEvertonLost
1998/99FA Cup SFNewcastleLost
1998/99League Cup SFWimbledonWon
1998/99League Cup finalLeicesterWon
2000/01FA Cup SFArsenalLost
2001/02League Cup SFChelseaWon
2001/02League Cup finalBlackburnLost
2007/08League Cup SFArsenalWon
2007/08League Cup finalChelseaWon
Table 3: Tottenham Hotspur’s 13 previous Semi-Final/Final appearances including and prior to 2008 League Cup Final

The first thing to spot is that there are six green bars and none with the caveat of lower league opposition. There is no doubt that Chelsea and Arsenal (in 2008) were better teams than us and likewise with Chelsea (2002). Leicester also finished above us for the three seasons before we beat them in 1999 and the 1991 victory over Nottingham Forest (our last FA Cup success) came against a backdrop of being knocked out of both domestic cups by the same opponent in 4 of the 6 seasons either side.

For those of you old enough to have lived through the cup glories of the early 80’s I’d be intrigued to get your take on what mental benefits were gained by the perpetual successes and ability to win semi-finals. Between 1981 and 1984 we won 6 from 7 of these ties resulting in 2 FA Cup’s and the 1984 UEFA Cup final. Why were we able to win these ties? Was it know-how, was it luck or was it just being a bit better than our respective opponent?

Whilst the previous comparisons identified failings when compared to the rest of the ‘top 6’ I have also compared our achievements against that next tier of clubs:

Figure C: THFC record in Semi-Finals and Finals compared to the other ‘similar sized’ clubs

What this shows is that we have far more frequently reached the latter stages of cup competitions than the clubs listed. It cements the view that whilst we are the Junior Partner of the so called ‘Big Six’ we are a long way ahead of the chasing pack using a variety of metrics.
My time parameter was 30 years – Everton and West Ham have only played in 13 ties between them in this period. Villa have been frequent semi-finalists but have not won anything since the 90’s. Leicester have a lot of green but look at their opponents and also consider that their successes in the 90’s were during the period that the League Cup was de-prioritised.

As the dust settles on yesterday’s somewhat predictable yet commendable defeat against a rampant Manchester City side what will change before our next big cup tie? How many more lessons can this group of players, and football club as a whole, learn in order to make things better next time.

When we hear the standard platitudes from our players through heavily managed club PR/Comms about ‘going again’ and ‘we’ll learn our lessons for next time’ you have to wonder what actual conversations are taking place. Maybe we need a Sports Psychologist to work with the squad; maybe we just need to win once….or perhaps we just need to hope that Manchester City and Chelsea get knocked out in the early stages and that we can capitalise?