Assistant head coach Cristian Stellini became the latest to issue an apology to Tottenham fans after Wednesday’s 1-0 loss to Sheffield United saw hopes of lifting a domestic trophy go up in smoke again.
Harry Redknapp, Andre Villas-Boas, Tim Sherwood, Maurico Pochettino, Jose Mourinho, Nuno Espirito Santo and Antonio Conte have all overseen cup exits since Spurs last trophy in 2008.
The north London side have come close on several occasions, losing finals to Chelsea, Manchester United and Manchester City, as well as suffering six semi-final exits.
Yet Spurs have spurned several golden opportunities since Juande Ramos lifted the Carabao Cup, with inexplicable collapses, team selections and performances allowing the trophy drought to continue.
Sportsmail takes a look back at the 10 most shambolic Spurs results since their last domestic trophy in 2008.
Tottenham suffered their 30th domestic cup exit since lifting the League Cup back in 2008
Tottenham assistant Cristian Stellini apologised to the fans after the club’s latest FA Cup exit
10. Tottenham 1-5 Chelsea – FA Cup semi-final – April 15, 2012
A thrashing at the hands of a hated rival is bad at the best of times, let alone in an FA Cup semi-final. The defeat came with a healthy dose of controversy which prevents it from featuring higher up the list.
Juan Mata was awarded a goal to put Chelsea 2-0 up at Wembley, despite television replays show that the ball had not crossed the line.
Gareth Bale pulled a goal back to give Spurs hope and potentially heighted their cause for complaint at the decision.
A late collapse, however, did not. Goals from Ramires, Frank Lampard and Florent Malouda saw Roberto Di Matteo’s side ease through to an FA Cup final against Liverpool.
The Blues were able to point to the final margin of victory to suggest the controversial goal may not have mattered.
Juan Mata was controversially awarded a goal as Chelsea thrashed Spurs at Wembley
9. Tottenham 2-3 West Ham – EFL Cup fourth round – October 25, 2017
Spurs came into the match fresh from a thumping 4-1 win over Liverpool, leading to Pochettino to declare his side were beginning to feel at home at their temporary Wembley home.
By contrast, West Ham had just been thrashed 3-0 by Brighton at the London Stadium.
Despite resting Harry Kane and Hugo Lloris, Spurs raced into a half-time lead with goals from Moussa Sissoko and Dele Alli.
A remarkable second half turnaround followed, as the Hammers scored three times in a 15 minute spell. Andre Ayew scoring twice in five minutes, before Angelo Ogbonna headed in the winner from a corner.
Pochettino questioned post-match whether his side ‘thought the job was done’ and bemoaned a lack of aggression and maturity.
Angelo Ogbonna scored the winner as West Ham came from 2-0 down to beat Spurs in 2017
8. Nottingham Forest 2-0 Tottenham – EFL Cup third round – November 9, 2022
One of two entries from this season’s campaign, with Spurs making a limp exit at the hands of Nottingham Forest from the Carabao Cup.
Forest entered the match at the bottom of the Premier League, but manager Steve Cooper still made nine changes. Antonio Conte surprised many with the strength of the selection with Kane captaining Spurs at the City Ground.
The hosts were dominant despite their heavily rotated side, with Renan Lodi and Jesse Lingard scoring at the start of the second half.
Spurs finished the match with just two shots on target, despite Forest’s Orel Mangala being sent off with 15 minutes remaining of the tie.
Antonio Conte named a strong starting team against Nottingham Forest but fell to defeat
7. Leeds United 2-1 Tottenham – FA Cup fourth round – January 27, 2013
Andre Villas-Boas claimed post-match he had no regrets about his team selection – a running theme – after being knocked out in the fourth round at Elland Road.
Villas-Boas had opted to leave Defoe, his only fit senior striker, out of the squad for the trip to face Neil Warnock’s Leeds United. Clint Dempsey was selected to lead the line by the Portuguese coach, who was still able to call upon Gareth Bale in his Spurs pomp.
Despite Leeds missing their top scorer Luciano Becchio, the hosts took an early lead after Luke Varney evaded Kyle Naughton and Steven Caulker.
Ross McCormack doubled the advantage in the second half for the mid-table Championship team, whose side included veterans Michael Brown and El Hadji Diouf.
Dempsey pulled a goal back for Spurs, before Villas-Boas threw on academy striker Jonathan Obika in desperate pursuit of an equaliser.
Luke Varney scored as Neil Warnock’s Leeds United overcame Spurs in the fourth round
6. Middlesbrough 1-0 Tottenham (AET) – FA Cup fifth round – March 1, 2022
The Premier League side were left with no excuses following their FA Cup exit to Middlesbrough last year.
Antonio Conte named a full strength team for their trip to the Riverside with Kane, Son and Dejan Kulusevski leading the attack.
Spurs only had to look to the previous round for their warning, after Championship Boro had shocked Manchester United at Old Trafford.
Conte’s side produced a lacklustre display during the 90 minutes, with a disallowed Harry Kane effort one of few clear cut chances created.
Middlesbrough gained the upper hand in extra time, with the hosts earning their reward when teenage substitute Josh Coburn fired beyond Lloris.
Josh Coburn scored an extra-time winner for Middlesbrough against a full-strength Spurs side
5. Sheffield United 1-0 Tottenham – FA Cup fifth round – March 1, 2023
Having bowed out with a full-strength side to Championship opposition last year, Wednesday’s team selection displayed a club failing to learn its lessons.
The absence of Cristian Romero and Kane from the starting eleven raised questions pre-match. As did the inclusion of Lucas Moura, who had made only two starts this season and is out of contract in the summer.
Cristian Stellini insisted the team selection for the game was fine, with Son Heung-min and Richarlison also starting in attack and an experienced defence.
The Blades opted to make eight changes with their Championship promotion push the priority, only increasing the embarrassment.
Stellini claimed post-match that Spurs had ‘missed an opportunity after Iliman Ndiaye’s winner, with another apology issued to the fanbase.
Having already seen Arsenal, Chelsea and Liverpool exit the competition prior to the tie, the limp exit has left Spurs supporters wondering again what could have been.
A potential home draw against Blackburn in the last eight for a start.
Iliman Ndiaye’s second half goal saw Sheffield United reach the FA Cup quarter-finals
4. Tottenham 1-1 Norwich (2-3 on pens) – FA Cup fourth round – March 4, 2020
This defeat is best remembered for the sight of Eric Dier clambering over seats at full-time to confront a supporter who had insulted him.
The confrontation came moments after Jose Mourinho’s side had been beaten 3-2 on penalties by Norwich, who at the time were propping up the Premier League table.
Erik Lamela struck the crossbar in the shootout while young striker Troy Parrott saw his penalty saved by Tim Krul. The home side’s exit display was summed up when loanee midfielder Gedson Fernandes saw a tame penalty saved by Krul.
Spurs had led the match through Jan Vertonghen’s first half header, only for Michel Vorm to spill a shot into the path of Josip Drmic, who equalised for the Canaries.
The veteran goalkeeper had survived a similar mistake in the first half after allowing a shot to slip through his grasp.
Mourinho’s decision to start Vorm had been questioned with the goalkeeper starting his first game in 18 months. Vorm had only been re-signed as cover after first choice Hugo Lloris suffered a dislocated elbow earlier in the campaign.
The defeat by Norwich was Vorm’s only appearance during the campaign. Remarkably the loss was not Spurs worst domestic cup exit of the season…
Eric Dier climbed into the stands in the aftermath of Spurs loss to Norwich in 2020
Michel Vorm’s error had allowed Norwich to equalise during the second half of the tie
3. Fulham 4-0 Tottenham – FA Cup fourth round – January 30, 2011
Tottenham fans were forced to endure a horror show at Craven Cottage in 2011 as Harry Redknapp’s side crashed to a 4-0 defeat in the FA Cup fourth round.
Redknapp named a strong starting eleven featuring much of the side which would later reach the Champions League quarter-finals, including Rafael van der Vaart, Luka Modric and Aaron Lennon.
The tie was over within the opening 25 minutes. Former Spurs midfielder Danny Murphy converting two penalties and Michael Dawson being shown a red card, before Brede Hangeland added a third from a corner.
The first-half capitulation was sealed when future Spurs midfielder Mousa Dembele made it 4-0.
Spurs survived the second half without further damage, although Aaron Hughes hit the crossbar and Hangeland saw a shot cleared off the line for the hosts.
Danny Murphy scored twice from the penalty spot as Fulham thrashed Tottenham in 2011
2. Colchester 0-0 Tottenham (4-3 on pens) – EFL Cup third round – 24 September, 2019
One of the first real signs the Maurico Pochettino era was crashing down came against Colchester.
Having been in the Champions League final just months prior, a visit to the League Two side should have represented a straightforward task.
Pochettino made 10 changes for the tie but Eric Dier, Davinson Sanchez, Dele Alli, Lucas Moura were among experienced stars to start in Essex.
As Spurs failed to make a breakthrough, Son Heung-min, Erik Lamela and Christian Eriksen were all summoned from the bench.
Pochettino’s side mustered just four shots on target as the match finished goalless.
Eriksen saw his penalty saved by U’s goalkeeper Dean Gerken and Lucas struck the crossbar, allowing Tom Lapslie to send the lowest ranked side in the competition through.
Spurs were beaten on penalties by League Two Colchester following a goalless draw
1. Tottenham 0-2 Portsmouth – FA Cup semi-final – April 11, 2010
While a defeat to League Two side was embarrassing, the context of the FA Cup semi-final loss to Portsmouth makes the defeat all the more painful for Spurs fans.
Harry Redknapp’s side came into the semi-final as the overwhelming favourites. After all, this was a Spurs team chasing Champions League qualification going toe-to-toe with Manchester City.
Pompey, on the other hand, had endured a miserable season after being deducted nine points for entering administration. Avram Grant’s side had seen their relegation from the Premier League confirmed just 24 hours before the semi-final.
A Spurs side including Jermain Defoe, Peter Crouch and Luka Modric produced 31 shots on goal during 90 minutes and extra-time but failed to beat David James.
Frederic Piquionne scored in extra time as relegated Portsmouth beat Spurs at Wembley
The inevitable happened in extra-time when Michael Dawson slipped on a heavily criticised Wembley surface, with Frederic Piquionne pouncing to score from close range.
Salt was poured into Spurs wounds when the former midfielder Kevin-Prince Boateng doubled Portsmouth’s lead from the penalty spot in the final minutes. The defeat is one of eight consecutive FA Cup semi-final defeats since Spurs last lifted the famous trophy in 1991.
Boateng would then miss a penalty in the final as Portsmouth were beaten 1-0 by Chelsea.
Spurs inexplicably followed up the shock defeat by beating Arsenal and Chelsea in consecutive Premier League matches en route to qualifying for the Champions League for the first time.