1987 -- Became the youngest player at 15 years, 6 months to win a main draw match at the US Open (d. McNamee) after taking a wild card...Also the youngest player to reach a tour SF (at 15 years, 7 months) in Scottsdale...Won the Las Vegas Challenger (d. J. Levine)...
1988 -- Captured his first Tour title in San Francisco (d. Kriek) at 16 years, 7 months...
1989 -- Became the youngest Roland Garros and Grand Slam champion (17 years, 3 months)...His thrilling five-set win for the title over Edberg was coupled with his RD 16 win over No. 1 Lendl, in which he served underhanded at one point after cramping but won 4-6, 4-6, 6-3, 6-3, 6-3 in a 4-hour, 37-minute match...Became the first American male to win the Roland Garros since Tony Trabert in 1955...After Roland Garros victory, climbed from 19 to No. 6 and later to 5 on Aug. 7, making him the youngest player ever to rank in the Top 5...
1990 -- Began the year with a fractured hip...Reached the QF in Tokyo and Roland Garros...Beat Wheaton, Agassi, Sampras and Jay Berger to claim the Canadian Open title, his lone title of the year...Helped the U.S. to Davis Cup title...
1991 -- Won his only title of the year in Birmingham (d. Raoux)...
1992 -- Won TMS Indian Wells and Miami...Reached US Open SF, losing to Edberg in a 5-hour, 26-minute marathon (longest in Open history)...Qualified for ATP Tour World Championship...
1993 -- Had five titles in seven finals...Enjoyed most of his success in Asia, winning four of five titles...Won all four matches to lead the U.S. to the Peugeot ATP Tour World Team Championship, and competed in his second consecutive year-ending World Championship...
1994 -- Won six titles in nine finals...Repeated title efforts in Jakarta (d. Rikl), Cincinnati (d. Edberg) and Beijing (d. Jarryd) and won for the first time in Philadelphia (d. Haarhuis), Hong Kong (d. Rafter) and Atlanta (d. Martin)...Qualified for his third consecutive ATP Tour World Championship...
1995 -- Reached his first ATP Tour World Championship final (d. Sampras in SF, l. to Becker) in Frankfurt ...Repeated titles in Hong Kong (d. Bjorkman), Atlanta (d. No. 1 Agassi) and Beijing (d. Furlan)... Compiled an 18-1 record in Asia...En route to the French final, defeated Stich in 4th RD and two-time defending champion Bruguera in SF...Won titles in Tokyo and Beijing...
1996 -- Joined Sampras and Ivanisevic as Top 10 finishers on the ATP Tour for fifth consecutive year...Won TMS Indian Wells (d. Haarhuis) and added titles during North America summer hard court circuit in Washington (d. W. Ferreira) and Los Angeles (d. Krajicek)...Reached his first Australian Open final (l. to Becker) and closed Grand Slam season by advancing to his first US Open final (l. to Sampras)...Jumped to career-high No. 2 ranking after Flushing Meadows and a victory would have put him at No. 1...Had 50-9 record on hard courts...Qualified for ATP Tour World Championship for fifth consecutive year...
1997 -- Captured five ATP Tour titles in as many finals and ranked No. 2 most of year...Began first four months with a 28-4 record...Put together win streaks of 11 and 10...Reached SF at Australian and US Opens...Helped U.S. into Davis Cup final with victories over Rafter and Philippoussis in SF tie...Qualified for ATP Tour World Championship for sixth consecutive year...
1998 -- Extended streak of winning at least one title to 11 straight years, longest active streak on Tour, with titles in Boston and Shanghai...Plagued by left knee and right wrist injuries during the year, resulting in first finish outside Top 20 since 1988...
1999 -- His streak of winning at least one ATP title for 11 consecutive years came to an end with his No. 50 ranking...His best results were SF in San Jose (l. to Mamiit), Shanghai (l. to Norman) and TMS Paris (l. to Safin), where he qualified into main draw...Also a QF at TMS Cincinnati (d. Safin, Pioline, No. 8 Corretja)...
2000 -- Won ATP title in Washington (d. Gambill) and joined Agassi as only active players to win a title in three different decades...Also reached final in Auckland (l. to Norman)...Best clay court event of season came in Atlanta, reaching SF (l. to Ilie)...At Roland Garros, lost to eventual champion Kuerten in four sets...At Wimbledon, lost to Popp 8-6 in fifth set in 2nd RD...On Asian circuit, reached QF in Hong Kong (l. to Henman) and SF in Shanghai (l. to Prinosil)...Reached 600 career match wins milestone in February...
2001 -- Finished outside Top 50 for first time since he was a 15-year-old in 1987...Made 14th consecutive Roland Garros appearance and lost to Roddick in five-set 2nd RD match...Best result of season came in Washington where he reached SF...After making his 15th consecutive US Open appearance, lost in 1st RD for first time in his career (l. to Lapentti)...Was forced to retire from a match (937 match streak) for first time in his career in 2nd RD encounter against Andrew Ilie in Hong Kong with back spasms.
2002 -- The 16-year veteran of ATP circuit slipped out of Top 100 for first time since he first emerged on tennis scene in 1987...Compiled a 7-18 match record and it was first time he's ever had a losing record and not won 10 matches in a season since '87...Won first Challenger title since Las Vegas in 1987 in Calabasas (d. Mamiit)...Played in his 55th Grand Slam tournament, most among active players and tied for third all-time...Reached at least 3rd RD at TMS Cincinnati for ninth time in his career before losing to eventual champion Moya...Reached 2nd RD at Wimbledon before losing to Schalken in four sets...Lost in 1st RD in eight of nine ATP events from February to June...Played last ATP event of 2002 in Tokyo where he defeated Clavet in 1st RD before losing to Hewitt...Suffered losses to Federer in 1st RD at Australian Open and 2nd RD at US Open...Compiled a 14-8 record at Challenger level, including a title in Calabasas (defeated Mamiit in final) and SF in Burbank.