Tottenham’s 2-1 defeat to Manchester United in the FA Cup semi-final on Saturday at Wembley was their eighth successive loss in the last four of the famous competition.
It is the worst run of losses at this stage and means they have not reached the final since 1991.
Here’s a look at their previous failings in the semi-finals over the last 25 years.
Arsenal 1 Tottenham 0 (1992-93)
The north London clubs met at Wembley at the semi-final stage of the FA Cup for the second time in three years and Arsenal gained revenge for their 1991 loss. Tony Adams’ second-half header was enough for the 10-man Gunners, who went on to beat Sheffield Wednesday in the final.
Tottenham 1 Everton 4 (1994-95)
Another run deep into the competition came to an end at the hands of a Daniel Amokachi-inspired Everton. The Nigerian scored twice, with Matt Jackson and Graham Stuart also notching at Elland Road. Jurgen Klinsmann scored a consolation for Spurs from the spot.
Newcastle 2 Tottenham 0 (1998-99)
Spurs did not get much more luck across the Pennines at Old Trafford as Newcastle downed George Graham’s side in extra-time. A goalless 90 minutes was followed by two Alan Shearer goals in the additional period as they suffered more semi-final heartache.
Arsenal 2 Tottenham 1 (2000-01)
Tottenham were back at Old Trafford two years later, bizarrely for another north London derby. Spurs were big underdogs but took an early lead through Gary Doherty. But Patrick Vieira levelled before the break and Robert Pires gave Arsene Wenger’s side a place in the final and bragging rights.
Tottenham 0 Portsmouth 2 (2009-10)
One of Spurs’ biggest disappointments was their Wembley clash with Portsmouth, who were on a fast-track to relegation from the Premier League. The league form went out of the window, though, as extra-time goals from Frederic Piquionne and Kevin-Prince Boateng sent Pompey through to the final.
Tottenham 1 Chelsea 5 (2011-12)
A London derby humbling came in 2012 as Spurs were blitzed by Chelsea. Quickfire goals either side of half-time put the Blues 2-0 up before Gareth Bale gave Tottenham hope. But three goals in the final 13 minutes saw Roberto Di Matteo’s men run wild.
Chelsea 4 Tottenham 2 (2016-17)
Chelsea were again the opponents as Spurs fell short again. They would have fancied going on to win when Dele Alli equalised at 2-2 early in the second half after Willian scored for Chelsea either side of Harry Kane’s goal. But it was Antonio Conte’s side who kicked on, booking a final spot thanks to goals in the final 15 minutes from Eden Hazard and Nemanja Matic.