Founded in 1905 Chelsea are not among the oldest clubs in English football, though they are certainly one of the most famous. Whilst they have long been a big club, a cursory glance at their list of honours shows that for a long time they were not one of the most successful sides around.
The majority of their success came after Roman Abramovich took over the club in 2003. That success includes plenty of FA Cup victories and that competition is our focus here as we take a look at all of their FA Cup triumphs, as well as the times when they did rather less well.
When Did Chelsea Last Win the FA Cup?
Chelsea, along with Arsenal, have been FA Cup supremos in the 21st century, although in the most recent of recent times they have suffered rather a lot of FA Cup heartbreak. Nonetheless, they last won the FA Cup in 2018 when they beat Man United 1-0 in front of more than 87,000 fans at Wembley.
FA Cup Finals
Unless stated all stats on this page are accurate ahead of the 2022/23 FA Cup campaign. The Pensioners, as was their more common nickname back then, first made the FA Cup final all the way back in the 1914/15 season. Their first win came some years later in 1970 but you can see a full summary of their FA Cup finals below.
In total they have made the showpiece game 16 times, coming out on top precisely 50% of the time. This total of eight FA Cup wins means they are joint third on the all-time winner’s list, level with Liverpool and Spurs but trailing Arsenal (14 wins) and Man United (12) by some distance.
|2022||Liverpool||Lost||0-0 (AET and 6-5 after penalties)|
|2007||Manchester United||Won||1-0 (AET)|
|1970||Leeds United||Won||2-1 (AET in replay, first game 2-2 AET)|
Stage of Elimination
16 finals is, of course, a superb return and means they are on their own in third place in terms of appearances in the big game. However, Chelsea have also frequently enjoyed good cup runs as well, even if they didn’t quite make the showpiece. A summary of their stage of elimination is shown below.
|Stage||Number of Times||Percentage|
|Qualifying Round 3||1||1%|
Please note that the percentages are rounded to the nearest percentage point. In addition, the format of the competition has changed over the years, most notably in the sense that earlier rounds were only played in those seasons prior to teams from the top two tiers entering the tournament at the third-round stage for the 1925/26 FA Cup.
Times Chelsea Won the FA Cup
The vast majority of Chelsea’s finals have come in the years after the Abramovich takeover, whilst five of their eight wins have come in that same period. Considering that a less-than-20-year period is a small slice of their overall history, it shows just how important the Russian’s ill-gotten finances were to the club. Below we have a little more detail about their eight wins, which we have divided into three separate eras.
Five FA Cups with Roman’s Rubles – 2007 to 2018
As noted above, Chelsea’s most recent FA Cup success came in 2018, with three consecutive final losses since then in 2022, 2021 and 2020. Even so, five finals in six years represents quite the feat! In 2018 it was Man United they got the better of, winning 1-0 thanks to an Eden Hazard penalty in the 22nd minute.
The Blues had a relatively straightforward route to the final, seeing off Norwich, Newcastle, Hull, Leicester and Southampton, though they were twice taken to extra time. Opponents United also had a nice run to the showpiece, only conceding a goal in the semis against Spurs, their first real test. The Red Devils probably had the better of the final, dominating possession and racking up 18 shots to Chelsea’s six. However, Hazard’s strike was decisive and gave Antonio Conte a first domestic cup as a manager. At the same time it condemned United boss Jose Mourinho to a first lost cup final in England, the Portugues ace having tasted glory in seven in a row previously.
Before this success their last FA Cup triumph came under Roberto Di Matteo in 2012. The Italian was acting as caretaker manager following the sacking of Andre Villas-Boas and did a superb job, landing the FA and Champions League double. The Blues beat Liverpool 2-1 in the final in what was a goal-packed FA Cup campaign for them. In the third round they put four past Portsmouth and notched five in the quarters and semis against Leicester and Spurs respectively. Again their opponents had more of the ball, more shots and four more shots on target but Blues fans will care not a jot about such stats.
John Terry also lifted the cup for Chelsea in 2010, his side again winning by a single goal, this time against Portsmouth. Man of the Match Didier Drogba got the game’s only goal after 59 minutes, and Carlo Ancelotti was the man in the Blues’ dugout. If they were lucky in the two finals to follow this, there can be no doubt this success was thoroughly deserved, Chelsea managing 24 shots in the game compared to Pompey’s two. One key talking point was the pitch, which John Terry said “ruined the final”, though how much difference it made to the result is debatable.
A year earlier Chelsea had also won the cup by a single goal, coming from behind to get the better of David Moyes’ Everton 2-1. The Merseyside outfit had the perfect start when Louis Saha scored the fastest goal in the 128-year (then) history of the FA Cup after just 25 seconds. Drogba equalised 20 minutes later before current Everton boss Frank Lampard scored what proved to be the winner with 19 minutes of the game remaining.
Abramovich is not known for his patience when it comes to managers and this time it was Dutch boss Guus Hiddink in the Chelsea hot seat. It wasn’t the most exciting clash in FA Cup history and saw just six shots on target. Yet again though, for many Chelsea supporters all that matters is the silverware and this victory was the club’s fifth in the competition.
Their fourth had come a couple of years earlier and, would you believe it, once again just a single goal separated the two finalists. Man United were the side to lose out, though this final had finished 0-0 after normal time. In the 116th minute Drogba again made the difference for his club and won yet more silverware for his manager, Mourinho. This was a very good United side too, with Wayne Rooney, Cristiano Ronaldo and the centre-back duo of Rio Ferdinand and Nemanja Vidic among their ranks. Chelsea edged the game, winning the FA Cup in the first final to be held at the new Wembley.
Two Wins at Turn of Millennium – 2000 & 1997
The Blues also made history by landing the first FA Cup of the new century and indeed millennium. On 20th May 2000 they beat Aston Villa (by a single goal, naturally), Roberto Di Matteo scoring the only goal of the game in the 73rd minute. Denis Wise was the man of the match in a team that included the likes of Gianfranco Zola and George Weah, whilst David James, Gareth Barry, Paul Merson and Dion Dublin were in the Villa starting XI.
This final was also the last to be played at the old Wembley, Chelsea clearly having a feel for when to make history. Villa played well, and possibly deserved to win but in the end it was Chelsea who claimed what was just their third ever FA Cup.
Their second was won just before the turn of the century in 1997. By their standards this was a fairly routine 2-0 win, this time over Middlesbrough. Di Matteo, who clearly had a taste for this famous old competition, was the man of the match and scored what was then the fastest goal in FA Cup final history after just 42 seconds. The unheralded Eddie Newton made sure of things with seven minutes to go.
It was Boro’s first ever FA Cup final in a strange season for them where they also lost the League Cup final (to Leicester) and were relegated from the Premier League. Bryan Robson was the Boro boss at the time, Ruud Gullit sitting in the Chelsea dugout. Robson’s former Man United teammate Mark Hughes claimed a fourth FA Cup success and partnered Zola up front.
Blues Land First FA Cup – 1970
There had been a long wait between Chelsea’s first and second FA Cup wins, 27 years in fact. And they had to fight very hard for it too, needing a replay (at Old Trafford) to see off a strong Leeds United side. The first game ended 2-2 in front of 100,000 fans and the replay wasn’t held until a full 18 days after the first game.
Chelsea won that one in front of a smaller but still sizeable crowd of over 62,000, needing extra time after the game finished 1-1. With the Blues skippered by Ron “Chopper” Harris and Leeds by Billy Bremner (who also had Norman “Bites yer legs” Hunter – where are the nicknames like that these days?!), a physical contest was always likely and that is exactly what we got. The two games were full of big tackles and aggression but plenty of skill too; this was the first time a replay had been needed in the final since 1912.
Chelsea’s Worst Upsets
As we have seen, the Blues have a super record in this competition, especially in the last 20 years or so. That does not mean they have been immune from bad results and upsets though. The summary of their stage of elimination above shows that they have failed to make the fifth round in almost half of the FA Cups they have entered. It is the big upsets that are our focus here though.
When it comes to the west London giants, there is little doubt that the worst defeat they have suffered came relatively recently in 2015, when Mourinho was at the helm. A fourth-round home time against third-tier Bradford should have been a doddle, especially with the hosts 2-1 up at the break. However, the West Yorkshire side hit back with three in the second half to win 4-2.
In addition, they also lost 3-1 away at Bristol City back in 1990. A season earlier there had only been a single division between the two teams but at kick-off there was a gulf between Chelsea, who would go on to finish fifth in the top flight, and third-tier City. There was also the 2008 loss to Championship side Barnsley, the Blues going down 1-0 in South Yorkshire when a semi-final place looked theirs for the taking. Aside from that Chelsea have generally avoided huge upsets, though their loss to Leicester in the 2021 final was certainly a fairly big surprise.