Who Is Running Spurs Transfer Window?

Milo and Steff get into how the structure of our backroom staff has changed and what it means for transfer activities, we’ll take a peek at the Euros so far, and report back on the week that was for N17 related news.

Men With Ven

Steff, Milo, and Gareth discuss our win over Burnley, Micky van de Ven winning games and player of the season awards, and the growth in both Spurs Women and the U21s who have both enjoyed a season of tremendous growth. We’ll even discuss what we want from Tuesday; isn’t it obvious?


Steff, Milo, and Ram talk bollocks about the North London Derby, discuss why Ben White is a twat, breakdown centimetres in modern football commesurate to arse sizes, discuss why Ben White’s fake tan is a twat, analyse those corners, discuss why we think Ben White is a tosser, declare our undying hatred of the Goons and express our personal belief that this journey is going to end up at an excellent destination, AND why Cuti Romero is our player of the season. Tis therapy with a grimace and a grin, join us…

Is Gascoigne Going To Have A Crack?

Steff, Gareth, and Milo discuss the forthcoming book by Gareth Dace about Spurs in the 90s titled, Is Gascoigne Going to Have A Crack? Spurs in the 90s, Magic, Mayhem and Mediocrity. For those who remember the era this is a belting conversation, for those learning about it, ’tis an entertaining education. We also pick our best 90s Spurs team, and learn the exact location of the physical book via Mr.Dace’s shipping GPS tracker! There’s also word of the next great Spurs dressing room DJ; you won’t guess who it is!

Is Gascoigne Going To Have A Crack – pre-order now

90’s Spurs – our earlier episode


Alfie Whiteman’s DJ set


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

Emotional Conte-nt

Steff, Milo and Ricky look back at Turf Moor lows, Elland Road highs, dynamic duos and Antonio Conte’s potentially menopausal media modulations which have seen him both violently throwing handbags and showering the squad with kisses within days. So not only do we drill into the matches that matter, this week you’ll also get a dose of aural HRT!

A Glitch In The Matrix

This week Steff, Ram, Ricky and Milo reveal the truth behind Spurs alarming home stand slump against Southampton and Wolves. The Matrix has a glitch. The 7 years olds in control need to stop squabbling every few minutes. James Brown needs to stop dragging out his encores and every Spurs supporter needs to stop worrying because none of this is real. So, for the TRUTH, as seen via an existential Tottenham lens, tune in right now.

King Power Hour and the Bridge of Sighs

This week, Steff, Milo, Ricky and James (aka Awesome) look back on midlands miracles, perfect pandemonium, bedsits & brothels, the horrors suffered by a horrifically assaulted Thiago (he’s OK BTW), and goals glorious goals from Berba to Bents with some proper Kaneage in the mix all underscored by Ghod. All this and Jay finds time to detail the top class Stamford Bridge steward presence…turn on, tune in and drop us a review.

Could U Be The Most Beautiful Goal In The World?

Hoddle vs Oxford (25 Apr 1987)

Berbatov vs Besiktas (19 Oct 2006)

Kane vs Arsenal (5 Mar 2016)

Bentley vs Arsenal (29 Oct 2008)