In a week dominated by events off the pitch, Tottenham go into this weekend’s Carabao Cup Final under the interim leadership of Ryan Mason, who has spent over two-thirds of his entire life at his boyhood club. He basically bleeds white and blue. But if he is to end the club’s long wait for a trophy, Spurs will have to overcome their recent cup final jinx, where they have lost four of five finals since the turn of the century.

When Tottenham ended Brentford’s hopes of a first-ever major cup final in January, they sat four points off the Premier League summit, level on points with Manchester City.

Now, as they prepare to face City at Wembley on Sunday, the first meeting of the sides in a major final since the famous FA Cup Final replay 40 years ago, the football landscape could not be more different.

As City look to complete the first part of a possible treble, Spurs in contrast will see the occasion as an opportunity to salvage some silverware from a season which despite starting promisingly, runs the risk of fizzling out. Following a run that resulted in only five points from five Premier League matches, as well as Europa League elimination, José Mourinho became the 10th managerial casualty of Daniel Levy’s reign as chairman. It’s a period which has yielded just a single trophy in 20 years.

Ironically, the Portuguese boasts a fine record in the League Cup’s various guises, overseeing four wins in four appearances. One of those successes came at the expense of Spurs in 2015, and now it falls on the shoulders of 29-year-old interim head coach Ryan Mason, who was in the Spurs central midfield that day, to try and improve on Tottenham’s relatively poor recent cup final record and end the club’s longest trophy drought since the 1950s.

Since their League Cup triumph in 2008, Spurs have reached three finals in all competitions but have finished on the losing side each time, without registering a single goal. No other Premier League team has reached more major finals in that period without winning at least one.

Spurs Cup Finals Since 2009

If you also take into account FA Cup semi-finals, Spurs’ record in domestic cup matches at the new Wembley, excluding ‘home’ matches played there during the building of their stadium, reads as played seven, won one, lost six.

We look back on Tottenham’s near misses since Jonathan Woodgate’s extra-time winner against Chelsea 13 years ago, as well as evaluate whether Mason’s Spurs can shake off the ‘Spursy’ tag to bring home some silverware in only his second game in charge.

2009: Paying the Penalty From Twelve Yards

A notable success in Spurs’ run to the Carabao Cup final this year was their penalty shootout victory over Chelsea in the fourth round. It was only the third time they had been successful in a shootout from the 12 they’ve participated in since 2000.

Perhaps the most notable of these occurred back in 2009, when they played out a 0-0 stalemate with Manchester United in the League Cup final, one year on from their last triumph in the same competition.

In the 12 months between both their final appearances, Spurs had seen considerable upheaval, both on and off the pitch. Following the departures of first-choice strike pairing Dimitar Berbatov and Robbie Keane in the summer of 2008, the team famously found themselves bottom of the league in early 2008-09, securing just two points from their first eight games. That winless run resulted in a change in the dugout, with Juande Ramos sacked and replaced by Harry Redknapp. The new man promptly resigned Keane, together with Jermain Defoe and Pascal Chimbonda, who had also left White Hart Lane in the previous 12 months.

By the time of the final, Spurs were up to 14th in the league but were still only two points off the drop zone and had only secured their place at Wembley as a result of two very late extra-time goals in the second leg of their semi-final against Burnley.

In contrast, United went into the game seven points clear at the top of the Premier League and despite rotating a number of their players for the final, they still fielded an XI which included Rio Ferdinand, Patrice Evra, Cristiano Ronaldo, Carlos Tevez and Paul Scholes. The man from Salford ended up pulling the strings in midfield during the game, attempting nearly double the number of passes (102) of any other player on the pitch.

Across the 120 minutes United demonstrated their superiority, creating better quality chances according to expected goals (1.3 vs 0.6), with Ronaldo and Tevez attempting more shots between them (14) than the rest of the Tottenham team combined. The Portuguese also came the closest to breaking the deadlock by hitting the post, but just one in five of United’s attempts ended on target and ultimately they were unable to breach the Spurs defence.

League Cup Final. Spurs vs. Manchester United xG shot map

When it came to the spot kicks, United were far more clinical from 12 yards than Spurs, with Jamie O’Hara seeing his attempt saved by Ben Foster and David Bentley firing his penalty wide. In contrast, United converted all four of their penalties to secure the trophy.

Whilst Spurs left Wembley empty handed, Redknapp helped Spurs secure their Premier League status. In the weeks following the final, they amassed 1.9 points per game from their remaining 12 matches to help secure a seventh-placed finish in the league. Given their awful start to the season, that was a remarkable achievement and it provided a springboard for the following campaign when they secured Champions League football for the first time.

2015: Chelsea Get Their Revenge

There was a sense of déjà vu for Tottenham’s next final six years later. As was the case in 2009, Spurs were being led by a new manager, Mauricio Pochettino, and had to overcome lower league opposition in the form of Sheffield United to reach the League Cup final. Again, they nearly let a comfortable lead slip, with the Blades coming back from 2-0 to equalise with 10 minutes of the second leg remaining. Spurs needed another late goal from Christian Eriksen to book their Wembley place. Such was their luck that they faced another team sitting comfortably at the top of the Premier League, Chelsea, who at that point under Mourinho had only lost three domestic games (including a shock FA Cup exit at home to Bradford City) in 2014-15.

Spurs came into the game as underdogs, and despite rockney legends Chas and Dave re-recording one of their 1980s chart staples, Hot Shot Tottenham,  they couldn’t inspire Pochettino’s team to glory.

With Mourinho’s side allowing the opposition the lion’s share of possession, a trait which Spurs fans would later get accustomed to, the North Londoners started the game brightly, with Eriksen hitting the bar in the opening 10 minutes. Playing behind Kane, the Dane was Spurs’ driving creative force, generating the highest expected assists output (0.35) of any player on the pitch. However, Chelsea gave away few opportunities inside their box and restricted their opponents to just two attempts on target.

In a game of few clear-cut chances, Spurs were undone by a goal from a set piece on the stroke of half-time from John Terry, before Diego Costa doubled the advantage in the second half.

League Cup Final. Spurs vs. Chelsea xG shot map

Following the final, the remainder of the season played out very similarly to that of the finalists in 2009, with the victors going on to win the Premier League title at the canter, whilst Spurs won half of their remaining league games to secure a top-five finish. It also saw Harry Kane reach 20 league goals in a season for the first time in his career, a milestone which he has gone on to hit in a further four Premier League seasons.

2019: Heartbreak in Madrid

In the years following their defeat to Chelsea, Spurs flourished under Pochettino as they challenged Leicester for the Premier League title in 2015-16 before finishing runners-up the following campaign, with the best home record in the competition (W17, D2, L0) during their final season at White Hart Lane. Their final points tally of 86 was also their best return since three points for a win was introduced into English football in 1981.

Spurs reached back-to-back FA Cup semi-finals in 2017 and 2018, but it wasn’t until the following year that they were to reach another final, defying all odds on the way.

After being on the brink of elimination in the UEFA Champions League group stages with just one point from their opening three matches, back-to-back home wins against PSV and Inter Milan followed by a point away to Barcelona saw Spurs progress to the competition’s knock-out stages. Their subsequent comfortable passage past Dortmund in the last 16 gave little indication of the drama that was to follow.

First, they overcame Manchester City on away goals thanks to a late VAR intervention that chalked off a late Raheem Sterling winner, before a remarkable turnaround in Amsterdam where they overturned a 3-0 deficit to Ajax in the final 35 minutes of the second leg – courtesy of a Lucas Moura hat trick – to reach their first-ever European Cup/Champions League final. It was a performance which suggested that the ‘Spursy’ tag could finally be consigned to the past, as they prepared for the biggest one-off game in the club’s history.

But in the final against Liverpool, any hopes they had of glory were dashed after just 23 seconds. Moussa Sissoko was penalised for a handball inside the box, and Mo Salah put away the resulting penalty.

In a match short on quality – reflected by the fact that Liverpool only successfully completed 64% of their attempted passes – Spurs actually created the better chances. Following the penalty, Jürgen Klopp’s side only managed a further two attempts on target, and their total non-penalty xG (0.53) was lower than Spurs (0.83). The three best chances of the match according to xG all fell to Dele Alli.

Champions League Final Spurs vs. Liverpool xG shot map

Of course, these numbers would have been influenced by the game state, as Liverpool defended a lead for over 88 minutes. Despite Divock Origi putting the game beyond Spurs’ reach late on, the 2019 Champions League final could go down as one of those ‘what might have been’ scenarios in Tottenham’s 139-year history, as they missed out on European football’s leading prize.

City Eye Revenge as Mason Looks to End Drought

In a remarkable coincidence, Spurs are going into another League Cup final with a new coach, having beaten lower league opposition in the semis, and now need to overcome the challenge of a runaway league leader to bring the trophy back to N17. It’s exactly the same scenario they faced in 2009 and 2015.

Given the circumstances of City’s Champions League elimination in 2019, you can expect Pep Guardiola’s team will be looking to avenge that defeat at Wembley on Sunday, particularly given that nine survivors of the starting XI who played in that second leg at the Etihad are still with the club.

Mason will be hoping that Harry Kane can return to full fitness following his injury, and the man himself may feel that he may have a point to prove having had relatively little impact in the cup finals he has featured in for Tottenham so far. In 180 minutes of cup final football, he has amassed just two attempts on target.

Harry Kane in Cup Finals for Spurs

Mason oversaw success in his first game in charge, seeing his side come from behind at half-time to beat Southampton 2-1. It was the first time this season that Spurs had won a game after trailing at the break – and only the second time it had happened in 15 instances since Mourinho replaced Pochettino in November 2019.

Wednesday’s match also saw Spurs record their most touches in the opposition box in a Premier League game this season (38), with Sergio Reguilón being notable for getting forward from left back. The Spaniard attempted the most passes (19) of any Spurs player in the attacking third, utilising the space created by Heung-Min Son cutting inside to generate the highest expected assist output on the night (0.12).

On the opposite side, Gareth Bale, restored to the starting line-up, created more chances in the game than any other Spurs player (three), as well as registering all of his side’s open-play shots on target (two).

Spurs’ lack of goal-bound attempts will be a concern going into Sunday. If we exclude penalties, the match against Southampton marked the ninth time in the Premier League this season that Spurs had attempted fewer than three attempts on target in a match. That further reinforces the importance of Kane’s recovery from the ankle injury he sustained against Everton, so that he can lead the Tottenham attack and provide the focal point to their front line.

For Mason, he goes into the weekend with an incredible opportunity to double the club’s trophy count in the 21st century. All that having been in the job less than a week. If he does, he’ll have contributed more silverware to the club than Messrs. Redknapp, Villas-Boas, Sherwood, Pochettino and Mourinho combined.

Around this time 30 years ago, the Tottenham first team squad entered the charts with a cup final single, titled ‘When the Year Ends in One,’ in reference to the six previous times they had won a competition in the opening year of a decade. That team promptly added to the club’s trophy cabinet with another FA Cup triumph.

Spurs fans will be hoping that the class of 2021 can emulate them and consign some of their more recent cup final heartaches to the annuls of history in the process.

Design by Matt Sisneros.