The 3 teams to play both an FA Cup & UCL final in the same season

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Roberto Di Matteo lifts the Champions League after Chelsea's win, Allianz Arena, Munich, May 2012

As Liverpool chase down what would be a remarkable quadruple haul of trophies, they know they have to face Chelsea in the FA Cup final just two weeks before their Champions League final clash with Real Madrid. Only three other teams have ever had to contend both in the same season before.

Winning even just one of these prestigious trophies is something most teams can only dream about, and to compete for both at the same time requires incredible quality, depth and a strong mentality.

With the games usually less than two weeks apart, winning one cannot be properly celebrated until the second game, making it a long mental and physical battle to try and bring both trophies home.

Liverpool have a long few weeks ahead, and they may look to the past to see how the three other teams fared when faced with both cup finals.

Manchester United – 1999

The only team to ever win the treble of the FA Cup, Champions League and Premier League, Manchester United’s 1999 side remains arguably their best ever.

They also had the unenviable task of the FA Cup final taking place just four days before their Champions League final in Barcelona.

Sir Alex Ferguson’s side made light work of Newcastle at Wembley, with goals from Paul Scholes and Teddy Sheringham securing a 2-0 victory before they crossed the channel.

The effects of such a turnaround were clearly felt, as they were behind for 85 minutes of their final clash with Bayern Munich, before Sheringham and Ole Gunnar Solskjaer came off the bench to win the game in injury time.

Ferguson clearly understood the pressure of playing two important games in such a short period, as he made five changes in his lineup after the FA Cup. Solskjaer started at Wembley, but came off the bench in Barcelona.

When you have as much attacking firepower as United did with Dwight Yorke, Andy Cole, Sheringham and Solskjaer, competing on multiple fronts isn’t too difficult.

Manchester United's Teddy Sheringham celebrating after scoring against Bayern Munich in the Champions League final. Nou Camp, May 1999.

READ: Teddy Sheringham talks replacing Eric Cantona and 11 days in May 1999

Chelsea – 2012

Chelsea found themselves in a wholly unprecedented situation when they finished sixth in the league, but set to travel to Wembley for the FA Cup final before a trip to Munich for the Champions League final.

They had started the season so badly that Andres Villas-Boas was sacked as manager, and Roberto Di Matteo assumed an interim role, but this turned out to be one of the greatest interim appointments ever.

The Blues breezed past Liverpool in the FA Cup final, with goals from Ramires and Drogba paving the way for a 2-1 win, but were then forced into a number of changes for the Champions League final.

John Terry, Ramires, Branislav Ivanovic and Raul Meireles were suspended, and three of them had started the FA Cup final. Ryan Bertrand, Gary Cahill and David Luiz came in to replace them in Munich, and did a stellar job as Chelsea beat Bayern Munich on penalties.

An agonisingly long 210 minutes, but there was glory in both competitions as a reward.

“That group of players deserved that success because they had been so successful at Chelsea,” Di Matteo stated after the final in Munich.

“That was an immense moment of their career to finally win the Champions League.”

Chelsea – 2021

Nine years later, Chelsea looked uncannily close to repeating their efforts of 2012.

Frank Lampard was sacked after a poor start to the season, and was replaced by Thomas Tuchel, who guided Chelsea to both finals in just a few months.

“As a manager, there is no time to waste. Honestly, now we compete for the FA Cup, we will get ready to compete at the highest level in Champions League, and we want to create a team that is absolutely no fun to play against,” Tuchel stated upon his appointment in January 2021.

And he was right, reaching both finals in an impressive manner.

However, Chelsea were stunned when Youri Tielemans scored a second-half stunner to give Leicester City a 1-0 victory at Wembley, and there wasn’t much optimism for the Champions League final two weeks later.

Chelsea travelled to Porto to face Manchester City, who were Champions of England.

Tuchel made three changes from the FA Cup final, which saw first-choice goalkeeper Edouard Mendy come in, as well as Kai Havertz replacing Hakim Ziyech.

This proved to be the difference between the two finals, as Havertz scored in the first half to give Chelsea a 1-0 win, becoming Champions of Europe for the second time.

Losing one final turned out to be the spark that won them the second one.

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