Professional Career
In 1989, McEnroe won the French Open Men's Doubles title and the Masters doubles title partnering Jim Grabb.
His first career singles final came in 1991 at Chicago, where he faced his brother John. John won the match 3–6, 6–2, 6–4. (This was the second time in tour history where two brothers faced each other in a tournament final, after Emilio Sánchez and Javier Sánchez met in the Madrid final in 1987.)
McEnroe's best Grand Slam singles performance came at the 1991 Australian Open, where he reached the semi-finals before being knocked-out by eventual-champion Boris Becker. (Commenting on his fellow semi-finalists, he told the press: "It's just like you all expected – Edberg, Lendl, McEnroe and Becker".) He was also runner-up in the men's doubles at the Australian Open that year, partnering his former Stanford team-mate David Wheaton.
McEnroe won the men's singles at the Sydney Outdoor Championships in 1995, to claim his first (and only) career singles title. He also had some notable Grand Slam singles results that year – beating Boris Becker in the first round of the Australian Open (before eventually losing in the fourth round), and then reaching the quarter-finals of the US Open where he lost to Becker in an epic four-hour and seven-minute four-set marathon.
But perhaps McEnroe's most memorable career moment comes as a catalyst of tennis legend (and older brother John's own rival) Jimmy Connors's legendary run during the 1991 U.S. Open. In the 1st Round of the 1991 U.S. Open, McEnroe led Connors two sets and 3–0 in the third set but Connors came back to win in 5 sets, walking off the court at 1:35 in the morning, after 4 hours and 18 minutes of play.
McEnroe retired from the professional tour in 1998.
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