Chelsea Football Club’s journey through the FA Cup has been marked by clashes, especially against rivals such as Manchester United, Arsenal, and Liverpool. These intense matches made many seasons memorable, adding to the rich history of English football.
Chelsea’s strife with Manchester City intensified in the past decade due to both clubs’ greater championship success, while the rivalry with Crystal Palace is mostly based on traditional London derbies that cause a lot of attention on Stake.com from hard core fans and football enthusiasts.
Chelsea vs. Manchester United: A Legendary Rivalry
The rivalry between Chelsea and Manchester United in the FA Cup brought some of the most famous matches in English football. The two clubs faced each other many times on their way to the finals, and several times they even played for the trophy.
1994 FA Cup Final: A Harsh Lesson
In the 1994 final, Chelsea faced powerful Manchester United, suffering a heavy blow of 4:0. This match put on full display in front of the world all the problems in the club and was a wake up call for Chelsea to start with radical changes.
In the first half of the 1990s, the Chelsea club was going through some rough patches, facing financial ruin caused by irresponsible decisions regarding the redevelopment of Stamford Bridge. Poor business moves affected everyone in the team, including players and the coaching staff. However, the team managed to reach the finals of the FA Cup in 1994 showing off a forgettable performance. In 1996, Chelsea hired player-turned-coach Ruud Gullit who turned their luck around. Chelsea came back the next year to the FA Cup finals, and won 2:0 against Middlesbrough. It was also the club’s first major trophy in 26 years. Middlesbrough, after the defeat in the League Cup final, was relegated from the Premier League.
2007 FA Cup Final: A New Era Begins
Chelsea was abruptly sold in 2003 to the Russian oligarch Roman Abramovich. The club was in debt and falling apart at the seams. After a short successful stint at the FA Cup, Chelsea continued to struggle financially. Abramovich, although not a very welcomed figure in the club, paid off the debt and brought in some world-class players, spending over 100 million pounds. Jose Mourinho was placed as the head coach after Ranieri didn’t deliver any trophies for the club. With Mourinho, Chelsea entered the golden era winning the Premier League, FA Cup and two League Cups.
In 2007, Chelsea beat Manchester United in the finals of the FA Cup, 1:0. This boosted the team’s morale, and they went on to become the fifth English team to win back-to-back league championships since the Second World War. The fans regained trust in the management and the players, and the club remained one of the favourites on Premier League betting platforms. The future looked bright again for Chelsea, with their new coach and an abundance of new, young players looking to make their mark in the most elite football league in the world.
2018 FA Cup Final: Redemption
Chelsea celebrated in 2009 as the FA Cup finals, beating Everton 2:1. However, for years after, the club had its major ups and downs. In 2018, Chelsea got their second chance, after losing to Arsenal the previous year, to lift the trophy at the FA Cup. The match was played at London’s Wembley Stadium, against Manchester United. After extra time, Chelsea won 1:0, redeeming itself from the 1994 devastating loss.
The match was played aggressively from both sides, with attackers falling in the penalty boxes several times without the referee calling faults. Finally, 22 minutes after the start, Hazard received a pass and made a run into Manchester United’s box, where he was fouled by Jones with a sliding tackle, who received the first yellow card of the game. This gave Chelsea a chance for a lead, and Hazard was strong and precise, earning the team another FA Cup.
Manchester United was statistically better in every segment of the match, with 63% of ball possession, 18 shots towards the goal, and nine corners. However, they also had two yellow cards, and many more faults that threw them out of balance and rhythm. Chelsea celebrated this win wholeheartedly, making up for the previous losses, and bringing fans another day of joy.
Chelsea vs. Arsenal: London Derbies on the Grand Stage
Chelsea and Arsenal, two London giants, had many intense matches in history. The ones that carve deep into the clubs’ memories are the FA Cup finals, one of the most cherished trophies in England.
2002 FA Cup Final: Arsenal’s Dominance
It was the fifteenth final for Arsenal and Chelsea’s seventh in the cup. The power struggle was too real this year, with both teams at the peak of their form reaching the third rounds in the Premier League. However, the match for Chelsea didn’t go as planned. Arsenal was flying high on the wings of victory against their rival Liverpool who beat them the previous year, beating them with a single goal. Chelsea, on the other hand, had less difficulty reaching the finals, beating Tottenham and Fulham on their way. So, when they faced power machine Arsenal, the outcome was less than desirable for Chelsea fans, 2:0.
The beginning of the century wasn’t so glorious for the club. Financial turmoil and uncertainty took their toll on everyone. Ranieri, their head coach at the time, was trying his best to get some sort of balance into the team, but missed opportunities plagued the club. On the verge of existence, the team felt the tension in the management. Ranieri was unfairly accused of being the main culprit for such poor results, when the lack of organization and discipline was visible on the field as well.
2017 FA Cup Final: A Setback for Chelsea
The match was played in a packed Wembley stadium on May 27th, 2017. Both teams were in their prime, winning multiple matches in different leagues before facing each other in the finals. From the start, the whole spectacle felt like a rematch and Chelsea’s chance to prove their power over Arsenal.
Shortly after the kickoff, in the fourth minute, Sanchez scored the first goal for Arsenal. However, this score will stay controversial for years to come. Arsenal was dominating possession and in the fourth minute, the ball fell to Alexis Sanchez from David Luiz’ headed clearance. The ball appeared to strike his outstretched hand but play continued. Aaron Ramsey was clearly on the offside. The assistant referee flagged, Ramsey stepped aside knowing that he was offside, and Sanchez scored. The goal stood, and referees determined that he wasn’t playing with his hands.
This threw off balance the whole Chelsea team, as they were scrambling to overcome the setback and focus on the next move. After a lot of chances, in the 76th minute, Diego Costa scored for Chelsea, for a 1:1 score. It gave fans faith that Chelsea could overturn the match, but all hopes diminished only two minutes later when Arsenal scored another goal.
The match finished 2:1, with Chelsea’s dream of getting back at Arsenal gone. Next year, Chelsea came back to the FA Cup finals beating Manchester United and partially redeeming themselves from the defeat against Arsenal.
Chelsea vs. Liverpool: Classic Encounters
Chelsea and Liverpool have shared several memorable FA Cup moments, with each team experiencing highs and lows.
2012 FA Cup Final: Chelsea’s Victory
In 2012, Chelsea was on its way to a perfect form, building up to the moment when they played in the FA Cup finals against Liverpool. Goals from Ramires and Didier Drogba gave the Blues a comfortable lead, and the team was just watching the clock. The late goal from Liverpool, towards the end of the game, woke up the team and they successfully ended the game 2:1.
Chelsea was participating in their eleventh final, they had previously won six and lost four. Liverpool was appearing in their fourteenth final, they had won seven times and lost six. With such statistics, Liverpool was a slight favorite, but Chelsea was closely following. Liverpool kept the ball in their possession most of the time, having 18 total shots at the goal, and 7 corner kicks. Chelsea was more passive, with less time with the ball, just 1 corner kick and 14 total shots on the goal, with only 6 on the target.
Regardless of the defensive game from the Blues, they managed to lift the trophy at the end.
2022 FA Cup Final: A Narrow Defeat
The second match in the FA Cup was much more tense than the one from a decade ago. Both teams entered the competition as Premier League clubs, in the third round. Chelsea had a slightly easier route to the finals, beating Crystal Palace in the semifinals 2:0. Liverpool, on their way to the finals, had to beat Manchester City in a thriller ending in 3:2.
Once the match started, both teams had plenty on the line. Liverpool was looking to redeem themselves, and Chelsea was set on securing their position in the rivalry where they would be the stronger, more powerful team. As the match went on, it was obvious that neither one would secure a win in the regular time. After extra time, the outcome was still unimpressive 0:0, so the match proceeded to penalties. The emotions were running high, with fans from both sides holding their breath right before the kick. In the end, Liverpool celebrated with 6:5.
To this day, that’s the score for the FA Cup when it comes to Liverpool Chelsea rivalry. It will be interesting to watch some future matches, where both teams are looking to assert their dominance.
Chelsea vs. Manchester City: A Modern Rivalry
Before the 2000s, Chelsea held the upper hand when it came to rivalry with Manchester City. In recent history, the City grew to become a force to reckon with in football with its huge investment in players and coaching staff. Overall, across all competitions, to this day, Chelsea still holds the lead with 71 wins to City’s 65. The balance shifted, and this year Manchester City played, and lost, the finals of the FA Cup against Crystal Palace.
- The 1986 Full Members’ Cup final was a memorable clash between the two giants of football. The match finished with an impressive score of 5:4 for Chelsea even though both teams had attacking tactics, and the power to win.
- The 2019 EFL Cup final was a pretty passive match, leading to no goals in the regular and extra time. The match was decided with penalties, with Manchester United grabbing the title with 4 : 3. However, the outcome is not the reason this match will stay in the history books of football. Chelsea’s goalkeeper refused to be substituted, causing controversy and confusion in the team. After the game, both Arrizabalaga and Sarri, the head coach, said that the situation was a misunderstanding with Sarri believing that Arrizabalaga was too injured to continue, but Arrizabalaga felt well enough to defend the goal. In any case, Chelsea lost this match with Ederson saving two goals from Jorginho and David Luiz.
- The 2021 UEFA Champions League final ended with Chelsea securing a 1:0 victory over Manchester City, with Kai Havertz scoring the only goal in the match, earning Chelsea their second Champions League title.
Since the 2021 Champions League final, Manchester City has been a dominating force, remaining unbeaten in ten consecutive matches against Chelsea. The last defeat was in the 2024/25 Premier League, when Manchester United won with 2:0.
Chelsea vs. Crystal Palace: The London Derby
Chelsea’s encounters with Crystal Palace are classic London derbies. Out of 67 meetings, Chelsea has won 38, drawn 17, and lost 12, showing clear dominance over the rival.
Premier League: Chelsea achieved league doubles over Crystal Palace in multiple seasons, including 2004/05, 2014/15, 2018/19 and 2021–22. It’s clear who is the favorite in every clash. However, Crystal Palace seems to be getting back on its feet, with the win in the FA Cup this year against Manchester City.
The 2025 Premier League match Chelsea and Crystal Palace played a 1:1 draw, giving a hint that Palace is slowly paving the way to the top teams in football.
Chelsea has had its ups and downs, changing coaches, managers, ownership and struggling with the financial side of the sport. In recent years, the club has been working tirelessly to blend young players with seasoned ones, in order to achieve balance in the game and restore the club to its former glory.
