1989 Wimbledon Championships – Men's Singles a Grand Slam tournament since the 1985 US Open final. The tournament also featured the first appearances of future champions Pete Sampras and Michael Stich in the main draw. Mats Wilander was about to complete the career Grand Slam in his career and losing to McEnroe in the quarterfinals. Ivan Lendl "(Semifinals)" 1989 Wimbledon Championships – Men's Singles Boris Becker defeated the defending champion Stefan Edberg in the final, 6–0, 7–6, 6–4 to win the Gentlemen's Singles tennis title at the 1989 Wimbledon Championships. The semi-final match between Ivan Lendl and eventual champion Becker became at the time the longest
2009 Wimbledon Championships – Men's Singles last time where an American male player reached the semifinals of a Grand Slam until Sam Querrey reached the semifinals of the 2017 Wimbledon Championships eight years later. Rafael Nadal "(Withdrew)" 2009 Wimbledon Championships – Men's Singles Rafael Nadal was the defending champion, but withdrew from the tournament due to knee tendinitis. In a repeat of the 2004 and 2005 finals, Roger Federer defeated Andy Roddick in the final, 5–7, 7–6, 7–6, 3–6, 16–14 to win the Gentlemen's Singles tennis title at the 2009 Wimbledon Championships for the sixth time. It became the longest men's singles final (in terms of