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The 81-year-old singer — who recently said he was taking a break from performing — joined in the celebrations to mark the 100th anniversary of Centre Court at the traditional British sporting event, by giving an acapella version of his hit Summer Holiday.
Sir Cliff appeared wearing a three-piece suit with purple and green stripes — the colours of Wimbledon Championships — and appeared in the Royal Box with a microphone as he attempted to lead the crowd in a sing-along.
Some of the audience could be heard clapping along with the Congratulations singer but the overall reaction was somewhat staid.
As Sir Cliff launched into a fourth verse of his summer song, he was cut off by applause from the crowd, bringing his performance to an early end.
The singer is a big fan of the tennis tournament, and before the retractable roof was installed on Centre Court in 2009, Sir Cliff would regularly lead spectators in impromptu sing-alongs when rain stopped play.
There was some negative reaction to the The Young Ones singer's latest performance on social media, with many viewers saying it had made them cringe.
One tweeted: "#cliffrichard lets be brutally honest. That “singalong that he did at #Wimbledon was one of the most cringiest things ever in the history of the world. NOBODY JOINED IN."
Another quipped: "Always wanted go to Wimbledon but genuinely terrified it would be when Cliff Richard was doing acapella again Not worth the risk."
And another said: "That Cliff Richard sing-along was a bit cringe. #Wimbledon."
But others defended Sir Cliff's performance.
Watch: Wimbledon celebrates Centre Court centenary on Sunday
One said: "@Wimbledon What a fantastic celebration of champions we saw on Centre Court today, Cliff Richard was awesome as ever and Sue Barker is a legend. Love the chat between her and Mac, with the joining of @BillieJeanKing it was wonderful. Thank you!"
Another declared: "So many rude comments about Sir Cliff Richard @Wimbledon. He is nearly 82, looks great for his age, still plays tennis-a game he loves- & he can still sing. Plus he is there to show his support for THE best tennis tournament - Wimbledon and celebrate 100 yrs of Centre Court!"
And a fan said: "Cliff Richard is an absolute legend. Probably the best singer to come out of the UK #Wimbledon."
Wimbledon is covered by the BBC, who invited Sir Cliff to take part in the centenary celebrations.
He said: ''Proud to be invited by the BBC and AELTC to participate in the Wimbledon Centenary Celebrations today. What an honour.''
In 2018 the singer sued the BBC for invading his privacy when they filmed a police raid on his house in 2014.
The raid was part of an investigation into historical child sex allegations. Sir Cliff was never arrested or charged.
Following his victory in the High Court, Sir Cliff was awarded £2m from the BBC to cover legal costs.
Watch: Sir Cliff comments on Murray and Raducanu exits from Wimbledon 2022