1985 Wimbledon Championships – Men's Singles record would eventually be broken by Michael Chang at the 1989 French Open. John McEnroe "(Quarterfinals)" 1985 Wimbledon Championships – Men's Singles John McEnroe was the defending champion but lost in the quarterfinals to Kevin Curren. Curren also defeated Jimmy Connors in the semifinal and became the first player ever to defeat both Connors and McEnroe in the same Grand Slam tournament. Boris Becker defeated Curren in the final, 6–3, 6–7, 7–6, 6–4 to win the Gentlemen's Singles tennis title at the 1985 Wimbledon Championships. Becker became the first unseeded player and the first German to win the Wimbledon singles
2008 Wimbledon Championships – Men's Singles 2008 Wimbledon Championships – Men's Singles Rafael Nadal defeated the five-time defending champion Roger Federer in the final, 6–4, 6–4, 6–7, 6–7, 9–7 to win the Gentlemen's Singles tennis title at the 2008 Wimbledon Championships. It was the longest championship match in Wimbledon history with play lasting four hours and 48 minutes, and with two rain delays. The event stretched over seven hours ending just before nightfall, and is widely considered to be the greatest match in tennis history. Roger Federer "(Final)" Gaël Monfils withdrew due to a shoulder injury. He was replaced in the draw by Lucky Loser Ilija