It’s one of those moments that has slipped into Wimbledon folklore—a rainy afternoon, a restless Centre Court crowd, and Sir Cliff Richard stepping in to save the day. The year was 1996, Pete Sampras was chasing yet another title, and Richard Krajicek was on the other side of the net.
But just a few games into their quarter-final, the heavens opened. This was long before Wimbledon’s retractable roof—back then, rain delays meant hours of waiting. As the downpour persisted, a tournament official had an idea: ask Cliff Richard, seated among the spectators, to keep the crowd entertained.
At first, Cliff hesitated. Wimbledon, after all, wasn’t set up for impromptu concerts. “I didn’t have a guitar, and I wasn’t sure how it would work,” he later told The Guardian. He agreed to a quick interview instead. But as it wrapped up, the host turned to the audience and said: “They would never forgive me if I didn’t ask you to sing.” And that was that—Cliff was on the spot, and as a seasoned performer, he knew there was only one answer.
He started, almost playfully, with Summer Holiday. The crowd roared. One song became several—The Young Ones, Bachelor Boy, a cover of Elvis’s All Shook Up, Living Doll, and, finally, Congratulations. It was entirely a cappella, which Cliff noted had its own charm: “It’s impossible to sing out of key, and the crowd sees the vulnerability of someone without any help.” The response was electric, with Wimbledon legends Martina Navratilova, Pam Shriver, Gigi Fernandez, and Virginia Wade even joining in as an impromptu backing group.
When the clouds finally parted, Cliff ended with a cheeky quip: “I never thought I’d actually play on Centre Court.”
That day wasn’t just a lucky coincidence. Cliff is a lifelong tennis fan and, since 1996, a member of the All England Club. His membership allows him not only to attend matches but to play on its courts and slip between venues via the private players’ tunnel. Ever since his unexpected concert, he’s been a regular feature in the stands—often dressed in one of his sharp suits, ready for the cameras to find him whenever the weather threatens.
In the end, it wasn’t just a rain delay that Cliff filled—it was a piece of Wimbledon history he helped create, one singalong at a time.