Let's be honest—when you think of Chelsea and the FA Cup, you think of Wembley drama, late winners, and that iconic blue ribbon around the trophy. The Blues have a rich history in England's oldest cup competition, and if you're building your fan media knowledge or just want to impress your mates at The Shed End, here's the full checklist of every FA Cup triumph. We're not just listing years—we're giving you the context, the key moments, and the players who made it happen.
1. The First Taste: 1970 – The Year It All Began
Chelsea's first FA Cup win wasn't just a victory—it was a statement. The 1970 final against Leeds United is still talked about as one of the toughest, most physical matches in English football history. After a 2-2 draw at Wembley, the replay at Old Trafford saw the Blues grind out a 2-1 win. David Webb scored the winner in extra time, and the club's love affair with the cup was born.
Key takeaway: This win set the tone for Chelsea's cup-fighting spirit. If you're researching the club's identity, this is your starting point.
2. The Double Decade: 1997 – A New Era Dawns
Fast forward 27 years, and Chelsea were back in the final. The 1997 win over Middlesbrough (2-0) was significant for two reasons: it was the club's first major trophy in 26 years, and it marked the beginning of the modern Chelsea. Roberto Di Matteo's goal after just 42 seconds remains the fastest in an FA Cup final. This victory laid the groundwork for the Abramovich era that followed.
Checklist item: When covering Chelsea's trophy history, always note this win as the bridge between the old guard and the new.
3. The Golden Era: 2000 – The Last of the Old Wembley
The 2000 final against Aston Villa was the last FA Cup final played at the old Wembley Stadium before its redevelopment. Chelsea won 1-0, with Roberto Di Matteo scoring again—this time in the 73rd minute. It was a fitting farewell to a legendary venue, and for Chelsea, it was a trophy that proved they could compete with the best.
Historical note: This win is often overshadowed by later successes, but for fans who remember the old Wembley, it's a cherished memory.
4. The Mourinho Masterclass: 2007 – First of the New Era
After the club's transformation under Roman Abramovich, the 2007 FA Cup win was Jose Mourinho's first in the competition. Chelsea beat Manchester United 1-0 in a tense final, with Didier Drogba scoring the winner in extra time. This victory was part of a double-winning season (alongside the League Cup) and solidified Mourinho's legacy as a cup specialist.
Tactical insight: Mourinho's Chelsea were known for their defensive solidity, but this final showed their ability to grind out results when it mattered.
5. The Double Double: 2009 – Ancelotti's First
Carlo Ancelotti's first season in charge (2009-10) was historic—Chelsea won the Premier League and FA Cup double. The FA Cup final against Portsmouth was a 1-0 win, with Didier Drogba scoring the only goal. This victory was part of a season where Chelsea scored 103 Premier League goals, a record at the time.
Player spotlight: Drogba's goal in this final was his third in FA Cup finals, cementing his reputation as a big-game player.
6. The Di Matteo Miracle: 2012 – A Season to Remember
Roberto Di Matteo took over as interim manager in March 2012 and somehow led Chelsea to both the FA Cup and Champions League. The FA Cup final against Liverpool was a 2-1 win, with goals from Ramires and Drogba. This victory was the first leg of an unforgettable double that defied all expectations.
Fan perspective: For Chelsea supporters, this win was emotional—Di Matteo, a club legend, delivered the trophy in the most unlikely circumstances.
7. The Conte Era: 2017 – A Dominant Display
Antonio Conte's first season in charge saw Chelsea win the Premier League and FA Cup double. The FA Cup final against Arsenal was a 2-1 victory, with goals from Victor Moses and Diego Costa. This win completed a remarkable turnaround after a disappointing 2015-16 season.
Tactical note: Conte's 3-4-3 formation was unstoppable that season, and the FA Cup final was a showcase of his tactical brilliance.
8. The Tuchel Triumph: 2021 – A Fans' Return
The 2021 FA Cup final against Leicester City was unique—it was the first major final with fans in attendance since the pandemic began. Chelsea won 1-0, with Youri Tielemans' goal for Leicester being the only one. Wait, that's wrong—Chelsea actually lost that final. Let me correct myself: Chelsea's most recent FA Cup win was in 2018 under Antonio Conte, not 2021. My mistake.
Correction: Chelsea's last FA Cup win was in 2018, beating Manchester United 1-0 in the final. Eden Hazard scored the winning goal from the penalty spot.
Quick Reference Table
| Year | Opponent | Score | Key Scorer | Manager |
|---|---|---|---|---|
| 1970 | Leeds United | 2-1 (replay) | David Webb | Dave Sexton |
| 1997 | Middlesbrough | 2-0 | Roberto Di Matteo | Ruud Gullit |
| 2000 | Aston Villa | 1-0 | Roberto Di Matteo | Gianluca Vialli |
| 2007 | Manchester United | 1-0 (aet) | Didier Drogba | Jose Mourinho |
| 2009 | Portsmouth | 1-0 | Didier Drogba | Guus Hiddink |
| 2010 | Portsmouth | 1-0 | Didier Drogba | Carlo Ancelotti |
| 2012 | Liverpool | 2-1 | Didier Drogba | Roberto Di Matteo |
| 2017 | Arsenal | 2-1 | Victor Moses | Antonio Conte |
| 2018 | Manchester United | 1-0 | Eden Hazard | Antonio Conte |
How to Use This List for Your Fan Media Content
If you're creating content for The Shed End Review, here's how to leverage this history:
- Match previews: Reference past FA Cup finals when covering Chelsea's cup runs.
- Player profiles: When writing about Cole Palmer or Enzo Fernandez, compare their cup performances to legends like Drogba or Hazard.
- Tactical analysis: Use the 2017 and 2018 wins as case studies for how Chelsea's system adapted to different opponents.
- Fan engagement: Ask your audience which FA Cup win was their favorite—the 1970 classic or the 2012 miracle?
Final Checklist for Your Article
- Include the 1970 win as the foundation
- Highlight the 1997 and 2000 wins as transitional moments
- Cover the Mourinho and Ancelotti eras
- Don't forget the Di Matteo miracle of 2012
- End with the Conte double in 2017-18
- Add a table for quick reference
- Link to related content like Chelsea trophy history list and Filip Jorgensen profile
The Bottom Line
Chelsea's FA Cup history isn't just a list of dates—it's a story of resilience, evolution, and moments that defined generations. From the mudbath of 1970 to the clinical efficiency of 2018, each win tells a different chapter of the club's journey. Whether you're a lifelong fan or new to the Blues, these victories are the backbone of Chelsea's identity. Now go share that knowledge with your audience—they'll thank you for it.
For more historical deep dives, check out our history and culture section.