Only three English clubs have contested more FA Cup Finals than Chelsea and even better, only two have achieved more wins with the Blues’ 8 triumphs having been bettered only by Arsenal and Manchester United.
|Season||Chelsea Result||Winner||Runner Up|
|2021-2022||Runner Up||Leicester City||Chelsea|
|1905-1906||Third Qualifying Round|
Chelsea FA Cup Wins
2017-2018: Chelsea 1–0 Manchester United
It could all have been over very quickly in 2018 as Chelsea just about edged past Norwich in a third-round replay, eventually winning on penalties. Comfortable wins against Newcastle and Hull followed though and after beating Leicester in extra-time in the quarter-finals, the Blues were back at Wembley.
Beating Southampton 2-0 in the semi’s, Antonio Conte’s men booked their final place against Manchester United in which an Eden Hazard penalty decided a very tight encounter to hand Chelsea their eighth FA Cup win in front of 87,000 people.
Things weren’t going terrifically well under Andre Villas-Boas in the league in 2011/12, but Chelsea’s FA Cup campaign got off to a great start with a 4-0 win against Portsmouth before QPR were taken care of at Loftus Road. Having beaten Birmingham and Leicester, Chelsea were drawn to play an intriguing semi-final against Tottenham under new boss Robert Di Matteo and it was to prove to be some spectacle!
Having enjoyed an upsurge in form in both this competition and the Champions League after the Italian’s appointment, the Blues hammered Spurs 5-1 in the semi-final to book a May date with Liverpool. After Didier Drogba put his side 2-0 up in the final Chelsea were coasting, though an Andy Carroll goal ensured things were nervy as the Blues held on for a 2-1 final success.
Carlo Ancelotti had already led his side to their third Premier League title by the time the Blues played Portsmouth in the 2010 FA Cup Final, that man Didier Drogba scoring the only goal of the game to ensure Chelsea landed the cup for the sixth time.
On their way to that Wembley success the Blues beat Watford (5-0), Preston (2-0), Cardiff (4-1), Stoke (2-0) and Aston Villa (3-0) in the semi-final in what was a very impressive cup campaign which meant the club won the trophy for the third time in four seasons.
With lots of toing and froing going on in terms of management; Luiz Felipe Scolari, Ray Wilkins and Guus Hiddink all taking their turn in the dugout after the FA Cup got going, Chelsea’s campaign to win back the cup could easily have been derailed and indeed a replay was needed to see off Southend United in round three.
Wins against Ipswich, Watford and Coventry however saw Chelsea head back to Wembley again where a late Didier Drogba goal sealed a semi-final win against Arsenal and, despite going 1-0 down to Everton inside a minute of the final, success was to come as goals from Drogba and Frank Lampard turned the game on its head and handed Chelsea a fifth FA Cup victory.
Jose Mourinho was still in his pomp as Chelsea manager when the 2007 FA Cup got going in earnest, his team securing victory in round three with a 6-1 win against Macclesfield Town to kick the campaign off. More comfortable wins came against Nottingham Forest and Norwich before a cup classic was played out at the Bridge, the Blues coming back from two-down to draw 3-3 with Tottenham in round six.
Having won the replay at White Hart Lane Chelsea headed to Old Trafford to take on Blackburn in the semi-finals, extra-time being needed with a late Michael Ballack goal and one from the tournament’s top-scorer Frank Lampard sending Blackburn out 2-1.
Lampard was man of the match in the final at Wembley as old foes Mourinho and Sir Alex Ferguson clashed, with Didier Drogba eventually settling a tense affair with the only goal of the game, just four minutes from the end of extra-time.
While more success was gained in the years to come, a squad containing Marcel Desailly, Gus Poyet, Roberto Di Matteo and Gianfranco Zola certainly looked good enough to win the cup in 1999-2000 and so it proved.
An utterly absorbing semi-final encounter at the old Wembley against Newcastle, a game in which Gus Poyet’s double was enough to eclipse Rob Lee’s header in a 2-1 win, meant momentum was hugely in the Blues’ favour as they faced Aston Villa in the final. Roberto Di Matteo was on hand again a cup final, scoring the only goal with 17 minutes left on the clock to seal the win.
Having not won a trophy for 26 years the Blues began this campaign with much expectation after Ruud Gullit had brought in some major stars to improve the squad, and they clearly had the stomach for knock-out football.
Wins against West Brom (3-0), Liverpool (4-2), Leicester (1-0 in a replay) and Portsmouth (4-1) took Chelsea to Highbury to face Wimbledon, a game they won comfortably 3-0 to set up a final appearance against Middlesbrough at Wembley.
The game proved to be famous for containing what was at the time the fastest goal in FA Cup Final history, Roberto Di Matteo scoring against Middlesbrough with just 43 seconds on the clock. Eddie Newton added another as the Blues beat Boro 2-0 to claim their first FA Cup win since 1970.
Dave Sexton was in charge when Chelsea claimed their first ever FA Cup triumph, beating Leeds United 2-1 in a replay at Old Trafford following a 2-2 draw at Wembley in the first final.
The Blues had to take care of Birmingham, Burnley, Crystal Palace, QPR and Watford along the way before David Webb could grab the famous extra-time goal that ensured Chelsea’s first FA Cup success with a team featuring Peter Bonetti and Peter Osgood among others.
Chelsea have made the semi-finals of the FA Cup twice in the Premier League era without progressing further, but their agonising defeats in the finals of both 2017 and 2002 are the ones that hurt the most.
Having waited until 14 minutes from time to grab an equaliser in the 2017 final against Arsenal, the Blues were undone by an Aaron Ramsey winner as Arsenal took the cup 2-1. The same teams contested the 2002 final at the Millennium Stadium in Cardiff, where Chelsea fought well but succumbed to a good Arsenal side who won 2-0 on the day.