If the 2025/26 season has been nothing short of a disaster for Chelsea, it could yet at least end on a high note.
The Blues are into the FA Cup final after a 1-0 victory over Leeds United in the semi; ironically, they were the opponent against whom Chelsea claimed their maiden FA Cup final triumph in 1970.
It will be the club’s 17th FA Cup final appearance in all, with only Arsenal and Manchester United having featured in more.
Chelsea’s eight FA Cup wins is also a record only bettered by the Gunners and the Red Devils, but then there’s another, less wanted symmetry: only Manchester United have lost more FA Cup finals than the Blues.
It’s a mixed bag of results alright, with the added factor that Chelsea have lost the last three FA Cup finals that they have contested.
So, we’re choosing to remain positive. Let’s instead look at Chelsea’s eight winning appearances in the FA Cup final.
Chelsea 2-1 Leeds United (1970)
Chelsea needed a replay to see off Burnley in the fourth round of the 1969/70 FA Cup, which was sandwiched in-between comfortable victories over Birmingham City (3-0) and Crystal Palace (4-1).
Goals from David Webb and Peter Osgood put the Blues two up after eight minutes against QPR in the quarter-finals, with Osgood going on to complete his hat-trick in an entertaining 4-2 triumph.
The semi-final with Watford could not have gone any smoother, as goals from Webb, Osgood and a brace from Peter Houseman carried Chelsea to a 5-1 victory.
A staggering 100,000 fans turned out for the final at Wembley Stadium, where Leeds United awaited. A feisty clash ended 2-2, which – back then – meant that a replay would be played.
Decamping to Old Trafford, Chelsea would eventually see off the resilient Leeds, with an extra time goal from Webb securing the Blues’ first ever FA Cup triumph.
Chelsea 2-0 Middlesbrough (1997)
It would be another 27 years before Chelsea would get their hands on the iconic trophy.
They would have to do things the hard way too, with a tough win over Liverpool in the fourth round and a replay required to get past Leicester in the fifth.
Portsmouth and Wimbledon were swept aside in the quarters and semis respectively, to set up a final against surprise package Middlesbrough.
The Blues were buzzing under Ruud Gullit, but it was still something of a shock when Roberto Di Matteo fired them ahead after just 45 seconds with a wonder strike – then, the fastest goal in FA Cup history.
Eddie Newton sealed the deal late on to secure Chelsea’s second FA Cup final triumph.
Chelsea 1-0 Aston Villa (1999/00)
That man Di Matteo was on the scoresheet again in the first FA Cup final of the new millennium.
A pretty straightforward route to the semi-finals saw Chelsea meet Newcastle at Wembley, where a brace from Gus Poyet was enough to see off a decent Magpies side.
Aston Villa were the opponents in what was a pretty tawdry final by all accounts, but Di Matteo’s goal was enough to separate the sides and secure Chelsea’s third FA Cup triumph and their second in the space of three seasons.
Chelsea 1-0 Manchester United (2006/07)
It was the first FA Cup final to be played at the ‘new’ Wembley Stadium… and a game that would begin Didier Drogba’s love affair with the trophy.
The Blues didn’t play top-flight opposition until the quarter finals, where goals from Andriy Shevchenko and Shaun Wright-Phillips saw off Tottenham in a replay.
Blackburn were beaten after extra time in the semis, which set up the final against Manchester United.
As was the case seven years before, this was a tight and cagey affair that ultimately finished 0-0 at the end of 90 minutes. That’s before Drogba stepped up to fire the winner in extra time… the first of what would be four goals in the FA Cup final in the Ivorian’s stellar career.
Chelsea 2-1 Everton (2008/09)
Di Matteo’s record for the fastest goal in an FA Cup final was beaten by Louis Saha, who fired Everton ahead after just 25 seconds.
Chelsea showed courage and resilience to come back from that, with Drogba equalising in the first half before Frank Lampard notched what would be the winner in the second.
Drogba had scored in the quarter and semi-finals victories over Coventry and Arsenal respectively.
Chelsea 1-0 Portsmouth (2009/10)
Few players have made themselves FA Cup icons quite like Didier Drogba.
He scored in the semi-finals in 2009/10 to carry Chelsea past Aston Villa, before once again stepping up in the final.
The Ivorian showed his versatility and class to curl home the free kick that defeated Portsmouth – that was his 37th goal of a campaign that also saw the Blues win the Premier League title.
Chelsea 2-1 Liverpool (2011/12)
Three FA Cup wins in four seasons, was it?
You better believe it, as Chelsea and Liverpool played out a humdinger in front of 89,000 at Wembley.
Ramires gave the Blues the lead, before Drogba – who else? – extended the lead.
Andy Carroll pulled one back for Liverpool in the second period, but it was another FA Cup icon for Chelsea – Di Matteo – that would have the last laugh; as interim head coach, he got to lift the trophy once more as his players held on for a 2-1 win.
Chelsea 1-0 Manchester United (2017/18)
Chelsea’s most recent FA Cup win, heading into the 2026 final, came in 2018.
This wasn’t the Blues’ finest hour at Wembley Stadium, but who cares? Eden Hazard, fouled by Phil Jones after 22 minutes, picked himself up and fired home the resulting penalty.
The fact that centre back Antonio Rudiger was named Man of the Match speaks volumes; this was a classic rearguard action under Antonio Conte, but one that helped Chelsea to their eighth FA Cup final triumph.