Ranking Chelsea's 5 biggest wins in FA Cup history

Chelsea Have Won The FA Cup 8 Times
Chelsea Have Won The FA Cup 8 Times

Chelsea have a rich history at both domestic and European levels. The Blues boast six Premier Leagues, two Champions Leagues, two Europa Leagues and eight FA Cups.

While European glory is more coveted, winning the FA Cup is no mean feat either. Coaches have to manage the squad well without losing focus on the Premier League campaign.

Chelsea have tasted success in the FA Cup

Chelsea recently entered the fourth round of the FA Cup after a resounding 5-1 win over Chesterfield. The Blues have been in 15 FA Cup finals and won on eight occasions. With the third-highest FA Cup titles to their name, they have always been a reliable side in the tournament.

Chelsea have had several historic matches during their FA Cup endeavors. We have ranked the five greatest victories the Blues have had while taking into consideration the opposition as well as the scoreline.

Without further ado, let's take a look at some of Chelsea’s memorable FA Cup wins:


#5 Chelsea vs Tottenham Hotspur (5-1)

Tottenham Hotspur v Chelsea - FA Cup Semi Final
Tottenham Hotspur v Chelsea - FA Cup Semi Final

Chelsea met Spurs in the 2012 FA Cup semi-final. The stage was set at Wembley and two formidable sides were looking to book their place in the final. However, not many would have expected the one-sided outcome of this match.

Didier Drogba opened the scoring in the 43rd minute with a rocket into the top corner. Juan Mata then doubled Chelsea’s advantage before Gareth Bale reduced the deficit. That was all Spurs could manage, however. Ramires scored Chelsea’s third before a brilliant free-kick by Frank Lampard made it four. Chelsea’s fifth and final goalscorer was Florent Malouda, who scored in extra time.

After giving Tottenham a drubbing at Wembley, Chelsea met Liverpool in the finals. The Blues emerged victorious once again with a scorline of 2-1 and lifted their seventh FA Cup. Didier Drogba found a winning connection at Wembley and his heroics were instrumental in their successful campaign.


#4 Chelsea vs Manchester City (5-1)

Chelsea v Manchester City - The Emirates FA Cup Fifth Round
Chelsea v Manchester City - The Emirates FA Cup Fifth Round

We now take a look at Chelsea’s fifth-round fixture against Man City in 2016. Both teams were below par in the Premier League that season and were hoping to do better in the FA Cup. Man City’s five teenage debutants had Chelsea liking their prospects.

Diego Costa opened the scoring for Chelsea after some lovely one-twos between Eden Hazard and Cesc Fabregas. David Faupala then equalized for City on his debut. This was all the joy the visitors would get, as Willian and Gary Cahill added Chelsea’s second and third goals respectively.

Hazard’s outstanding free-kick then added another in Chelsea’s favor. City were completely blown away and Bertrand Traore scored late into the second half to make it five.

Chelsea entered the sixth round on a high but were knocked out by Everton. It was a disappointing end to Chelsea’s FA Cup run. The Blues eventually finished 10th in the league and had a domestic campaign to forget.

#3 Chelsea vs Watford (5-0)

Chelsea v Watford - FA Cup 3rd Round
Chelsea v Watford - FA Cup 3rd Round

Chelsea faced Watford in the third round of the 2010 FA Cup. Daniel Sturridge starred in this game for a Chelsea side who were missing both Drogba and Nicolas Anelka. The Blues may have been missing their front men but were unstoppable in attack.

They began the game in relentless fashion, with Sturridge scoring in the fifth minute. Joe Cole’s cross in the 15th minute struck Watford’s Eustace who had to concede an own goal. Malouda added to Watford’s misery soon after and Chelsea went into halftime with a three-goal lead. Lampard’s signature long-range stunner and Sturridge’s well-taken goal increased Chelsea’s advantage to five.

Chelsea eased through the remaining fixtures and entered the finals. The Blues were hoping to successfully defend the title and indeed did so with a 1-0 win over Portsmouth in the final. They also dominated the Premier League and won the domestic double that season.


#2 Chelsea vs Macclesfield ( 6-1)

Shevchenko Celebrating With Teammate Frank Lampard
Shevchenko Celebrating With Teammate Frank Lampard

After winning the Premier League in the 2005-06 season, Chelsea looked set to add more trophies to their collection the following year. Their FA Cup journey started against Macclesfield. With Drogba missing, Lampard rose to the occasion as he often did for the Blues.

The Chelsea captain opened the scoring after just 15 minutes. John Murphy provided a shock equalizer for Macclesfield in the 40th minute, but it was short-lived joy. Lampard equalized almost immediately and then scored a penalty to complete his hat-trick. Shaun Wright-Phillips, John Obi Mikel and Carvalho were on the scoresheet as well.

The resounding victory set the stage for Chelsea’s FA Cup journey which eventually ended in them lifting the trophy. The Blues faced Manchester United and defeated them 2-1 in a final which went all the way to extra time.


#1 Chelsea vs Ipswich (7-0)

Chelsea v Ipswich Town - FA Cup 3rd Round
Chelsea v Ipswich Town - FA Cup 3rd Round

The 2011 FA Cup clash between Chelsea and Ipswich at Stamford Bridge saw the home side achieve a resounding victory. Chelsea started their title defense in style in what was a day to forget for Ipswich.

Salomon Kalou started things off for Chelsea by tapping in Anelka’s effort just after 30 minutes. Sturridge quickly added a second and an unfortunate Carlos Edwards own goal made it 3-0 to Chelsea. The majority of the second half was smooth sailing for the visitors, with quickfire goals from Anelka and Sturridge. Lampard added to Ipswich’s misery with two goals towards the end.

The Blues booked their place in the fourth round of the FA Cup after this statement victory. However, Chelsea had a disappointing title defense and their progress was halted by Everton. The tie was decided over two games and Everton eventually won 4-3 on penalties.

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