1988 -- Won the Vina del Mar Challenger (d. Duncan) and then turned pro...Reached first Tour SF in Charleston and advanced to SF in Stockholm...
1989 -- Beat Agassi for first career Top 10 win at French Open en route to the RD 16...Rallied from a 1-2 sets deficit to defeat Edberg in the Basel final, giving the 19-year-old his first Tour singles title...Captured first Tour doubles title in Rome (w/Sampras) and played in doubles Masters...
1990 -- Best showing SF in Indian Wells and QF in seven other Tour stops...Won second doubles title in Hamburg (w/Bruguera)...
1991 -- Won three titles, including Key Biscayne and French Open (d. Agassi in first all-American final since 1954)...Also a runner-up at U.S. Open and ATP Tour World Championship, SF six times and QF at Wimbledon...Improved ranking from 25 to No. 2...Became first American to be ranked No. 2 since J. McEnroe in 1985...
1992 -- Became the 10th player to rank No. 1 in ATP Tour Rankings on Feb. 10 after his runner-up showing in San Francisco...Won Australian Open, Tokyo-outdoor, Hong Kong, Rome and second consecutive French Open...Career-best winning streak stretched to 25 matches before 3rd RD loss at Wimbledon (l. to Olhovskiy)...Reached four finals, including ATP Tour World Championship (l. to Becker)...Clinched U.S. victory over Switzerland in Davis Cup final with four-set win over Hlasek...
1993 -- Won five titles for the second year, with runner-up efforts in Hong Kong, French Open and Wimbledon...Successfully defended titles at Australian Open and Rome...Ranked No. 1 for 17 weeks...
1994 -- Finished out of Top 10 and did not win a title for first time since 1990...Runner-up at Nice (l. to Berasategui) and Lyon (l. to Rosset)...Played in two U.S. Davis Cup ties, posting a 4-0 record against India and The Netherlands, including a fifth and decisive victory over Eltingh in QF...
1995 -- Returned to the Top 10 for the fourth time in the last five years...Won four titles in five finals, all on different continents - Adelaide (Australia), Scottsdale (North America), Tokyo-outdoor (Asia) and Basel (Europe)...Reached QF at the Australian Open, losing a five-set marathon to Sampras...Helped the U.S. to a 4-1 opening-round Davis Cup win over France in February...Reached U.S. Open SF (l. to Sampras)...Reappeared in the Top 10 (from 11 to No. 9) after the Open for the first time since Aug. 15, 1994...Appeared in his fourth ATP Tour World Championship...
1996 -- Finished out of Top 25 for first time since his rookie season in 1988...Ranked in Top 10 most of year until falling out after U.S. Open where he withdrew because of a right knee injury...Missed his first Grand Slam tournament since 1989 French Open, a streak of 30 consecutive Grand Slams played...Injury persisted and he missed two months...Reached QF at Australian Open (l. to Agassi) and played in first U.S. tournament of year in Philadelphia and won lone title (d. Woodruff)...SF effort in Barcelona (l. to Rios) and QF at French Open (l. to Sampras)...His 45 singles matches played were fewest since 1988 when he played 36...
1997 -- Captured three titles in as many finals: Doha (d. Henman), Los Angeles (d. Enqvist) and Beijing (d. Gustafsson)...Helped U.S. to Davis Cup SF with five-set triumph over Siemerink (rallied from 0-2 sets deficit for first time and saved one match point)...Went 7-4 vs. Top 10 opponents and compiled 27-10 record on hard and 6-4 on clay...
1998 -- Won his lone title of season in his hometown of Orlando, defeating long-time rival Chang in three sets...Fell to No. 118 on Oct. 12 before climbing back with SF in Singapore and QF in Bogota and Santiago, both on clay...Helped U.S. to 3-2 1st RD Davis Cup victory over Russia by beating Safin 6-4 in fifth set...One of only four Americans to win a five-set match in fifth and decisiver rubber, joining Chang, John McEnroe and Don Budge.
1999 -- The American rebounded back from a disappointing 1998 season...Improved his match wins total by 10 and jumped over 40 ranking positions...In January, retired for first time in a Grand Slam tournament in 3rd RD of Australian Open (vs. Kafelnikov) due to left groin pull...One month later, advanced to his lone ATP Tour final of year in Memphis (l. to Haas), where he suffered a left foot sprain in SF but played in title match despite injury...Afterward, jumped from 69 to No. 45 on Feb. 22...One of biggest moments of his career came in 1st RD Davis Cup tie in Birmingham, England where he lifted U.S. to a dramatic 3-2 victory over Great Britain...Posted a 4:12 five-set victory over No. 7 Henman in opening match and beat No. 11 Rusedski 8-6 in fifth set in decisive match, which lasted 3:46...During claycourt circuit, reached QF in Orlando and SF in Atlanta...On grass, advanced to 4th RD at Wimbledon for first time since '93 when he reached final...Provided more drama in England, defeating No. 10 Moya in 2nd RD in five sets and Schalken 13-11 in fifth set of 3rd RD in 4:25...Fell short to Henman in 4th RD, losing 9-7 in fifth set in second-longest singles match (4:30) in Wimbledon Open Era history...Posted 4-1 record in five-set matches during season...In August, beat No. 5 Henman in 2nd RD of Super 9 in Montreal en route to QF, losing to eventual winner Johansson...Closed out year with 6-3 mark during European indoor circuit, reaching 3rd RD in Lyon, 2nd RD in Stuttgart and QF in Paris (d. Moya, No. 9 Enqvist, l. to Safin)...Played consistently on all surfaces --16-13 on hard, 6-4 on clay, 5-2 on carpet, 4-2 on grass.