McEnroe struggled to regain his form after his
1986 sabbatical. He lost, for example, three times in
Grand Slam tournaments to
Ivan Lendl, losing straight-set quarterfinals at both the
1987 U.S. Open and the
1989 Australian Open and a long four-set match, played over two days, in the fourth round of the
1988 French Open.
Nevertheless McEnroe had several notable victories in the final years of his career.
In
1989, McEnroe won a record fifth title at the
World Championship Tennis Finals (the championship tournament of the WCT tour, which was being staged for the last time), defeating top-ranked Lendl in the semifinals. At
Wimbledon, he defeated
Mats Wilander in a four-set quarterfinal before losing to
Stefan Edberg in a semifinal. He won the RCA Championships in
Indianapolis and reached the final of the
Canadian Open, where he lost to Lendl. He also won both of his singles rubbers in the quarterfinal
Davis Cup tie with
Sweden.
Controversy was never far from McEnroe, however. In his fourth round match against
Mikael Pernfors at the
1990 Australian Open, McEnroe was disqualified for swearing at the umpire, supervisor, and referee. He was warned by the umpire for intimidating a lineswoman and then docked a point for smashing a racket. McEnroe was apparently unaware that a new Code of Conduct, which had been introduced just before the tournament, meant that a third code violation would not lead to the deduction of a game but instead would result in immediate disqualification. So when McEnroe unleashed a volley of abuse at umpire Gerry Armstrong, he was defaulted.
Later that year, McEnroe reached the semifinals of the
U.S. Open, losing to the eventual champion,
Pete Sampras. He also won the
Davidoff Swiss Indoors in
Basel, defeating
Goran Ivanišević in a five-set final. The last time McEnroe was ranked in the world top ten was on October 22, 1990, when he was ranked 9th. His end-of-year singles ranking was 13th.
In
1991, McEnroe won the last edition of the Volvo Tennis-Chicago tournament by defeating his brother
Patrick in the final. He won both of his singles rubbers in the quarterfinal Davis Cup tie with
Spain. And he reached the fourth round at Wimbledon (losing to Edberg) and the third round at the U.S. Open (losing to
Michael Chang in a five-set night match). His end-of-year singles ranking was 28th in the world.
In
1992, McEnroe defeated third-ranked
Boris Becker in the third round of the Australian Open 6-4, 6-3, 7-5 before a sell-out crowd. In the fourth round, McEnroe needed 4 hours 42 minutes to defeat ninth ranked
Emilio Sanchez 8-6 in the fifth set. He lost to
Wayne Ferreira in the quarterfinals. At
Wimbledon, McEnroe reached the semifinals where he lost in straight sets to the eventual champion
Andre Agassi. McEnroe teamed with
Michael Stich to win his fifth Wimbledon men’s doubles title in a record-length 5 hour 1 minute final, which the pair won 5-7, 7-6, 3-6, 7-6, 19-17. At the end of the year, he teamed with Sampras to win the doubles rubber in the Davis Cup final, where the U.S. defeated
Switzerland 3-1.
McEnroe retired from the professional tour at the end of
1992. He ended his singles career ranked 20th in the world.