| Singles | |
|---|---|
| 1999 Sybase Open | |
| Champion |  Mark Philippoussis |
| Runner-up |  Cecil Mamiit |
| Score | 6–3, 6–2 |
| Draw | 32 (4Q / 3WC) |
| Seeds | 8 |
Andre Agassi was the defending champion, but was defaulted in his second round match against Cecil Mamiit for swearing at a line judge. [1]
Mark Philippoussis won the title, defeating Mamiit 6–3, 6–2 in the final. [2]
Pete Sampras (semifinals, withdrew because of an ankle injury) [3] Andre Agassi (second round, defaulted) Mark Philippoussis (champion) Michael Chang (semifinals)
Mariano Puerta (first round) Jan-Michael Gambill (first round) Mariano Zabaleta (first round)
Ramón Delgado (second round)| Semifinals | Final | ||||||||||||
| 1 | Pete Sampras | ||||||||||||
| 3 | Mark Philippoussis | w/o | |||||||||||
| 3 | Mark Philippoussis | 6 | 6 | ||||||||||
| Q | Cecil Mamiit | 3 | 2 | ||||||||||
| 4 | Michael Chang | 6 | 3 | 4 | |||||||||
| Q | Cecil Mamiit | 3 | 6 | 6 | |||||||||
| First round | Second round | Quarterfinals | Semifinals | ||||||||||||||||||||||||
| 1 | P Sampras | 6 | 6 | ||||||||||||||||||||||||
 G Blanco | 4 | 4 | 1 | P Sampras | 7 | 6 | |||||||||||||||||||||
| M Rodríguez | 6 | 62 | 6 | M Rodríguez | 5 | 3 | |||||||||||||||||||||
| Q |  A Hernández | 4 | 77 | 3 | 1 | P Sampras | 7 | 6 | |||||||||||||||||||
| Q |  B Karbacher | 6 | 6 | Q | B Karbacher | 5 | 3 | ||||||||||||||||||||
 S Koubek | 3 | 2 | Q | B Karbacher | 6 | 65 | 6 | ||||||||||||||||||||
 S Lareau | 6 | 6 | S Lareau | 3 | 77 | 3 | |||||||||||||||||||||
| 7 | M Zabeleta | 2 | 1 | 1 | P Sampras | ||||||||||||||||||||||
| 3 | M Philippoussis | 62 | 7 | 6 | 3 | M Philippoussis | w/o | ||||||||||||||||||||
 S Sargsian | 77 | 5 | 3 | 3 | M Philippoussis | 6 | 6 | ||||||||||||||||||||
| J Courier | 4 | 64 |  J van Lottum | 2 | 1 | ||||||||||||||||||||||
| J van Lottum | 6 | 77 | 3 | M Philippoussis | 6 | 3 | 77 | ||||||||||||||||||||
| Q |  R Agénor | 6 | 2 | 3 | WC | J Gimelstob | 2 | 6 | 60 | ||||||||||||||||||
| WC | C Woodruff | 2 | 6 | 6 | WC | C Woodruff | 4 | 63 | |||||||||||||||||||
| WC | J Gimelstob | 6 | 78 | WC | J Gimelstob | 6 | 77 | ||||||||||||||||||||
| 6 | J-M Gambill | 3 | 66 | ||||||||||||||||||||||||
| First round | Second round | Quarterfinals | Semifinals | ||||||||||||||||||||||||
| 5 | M Puerta | 2 | 6 | 3 | |||||||||||||||||||||||
 C Ruud | 6 | 4 | 6 | C Ruud | 6 | 77 | |||||||||||||||||||||
| C Costa | 6 | 4 | 4 | WC | P Goldstein | 1 | 64 | ||||||||||||||||||||
| WC | P Goldstein | 4 | 6 | 6 | C Ruud | 1 | 5 | ||||||||||||||||||||
| F Squillari | 6 | 3 | 6 | 4 | M Chang | 6 | 7 | ||||||||||||||||||||
| A Portas | 1 | 6 | 2 | F Squillari | 4 | 65 | |||||||||||||||||||||
 F Meligeni | 3 | 2 | 4 | M Chang | 6 | 77 | |||||||||||||||||||||
| 4 | M Chang | 6 | 6 | 4 | M Chang | 6 | 3 | 4 | |||||||||||||||||||
| 8 | R Delgado | 5 | 6 | 7 | Q | C Mamiit | 3 | 6 | 6 | ||||||||||||||||||
 B Steven | 7 | 4 | 5 | 8 | R Delgado | 2 | 3 | ||||||||||||||||||||
| S Campbell | 3 | 6 | 5 | M Woodforde | 6 | 6 | |||||||||||||||||||||
| M Woodforde | 6 | 3 | 7 | M Woodforde | 65 | 6 | 3 | ||||||||||||||||||||
| Q | C Mamiit | 2 | 6 | 7 | Q | C Mamiit | 77 | 4 | 6 | ||||||||||||||||||
 K Carlsen | 6 | 3 | 5 | Q | C Mamiit | 0 | 6 | ||||||||||||||||||||
| T Woodbridge | 2 | 1 | 2 | A Agassi | 6 | 6d | |||||||||||||||||||||
| 2 | A Agassi | 6 | 6 | ||||||||||||||||||||||||
Two-time defending champion Pete Sampras defeated Andre Agassi in the final, 6–3, 6–4, 7–5 to win the gentlemen's singles tennis title at the 1999 Wimbledon Championships. It was his record-breaking sixth Wimbledon title and record-equalling twelfth major singles title overall. Sampras' victory over Agassi in the final is often cited as one of the greatest performances in a Wimbledon final. However, despite his victory, Sampras lost the world No. 1 ranking to Agassi, who had recently won the French Open and was attempting to complete the Channel Slam.
Andre Agassi defeated Todd Martin in the final, 6–4, 6–7(5–7), 6–7(2–7), 6–3, 6–2 to win the men's singles tennis title at the 1999 US Open. It was his second US Open title and fifth major title overall. With the win, Agassi returned to the world No. 1 singles ranking, ultimately ending Pete Sampras' record streak of six year-end No. 1 rankings.
Andre Agassi defeated the defending champion Yevgeny Kafelnikov in the final, 3–6, 6–3, 6–2, 6–4 to win the men's singles tennis title at the 2000 Australian Open. It was his second Australian Open title and sixth major title overall. It was also Agassi's fourth consecutive major final, making him the first man to reach all four major finals consecutively since Rod Laver in 1969. With the win, Agassi became the reigning champion at three of the four majors, missing only the 1999 Wimbledon Championships.
Andy Roddick defeated Juan Carlos Ferrero in the final, 6–3, 7–6(7–2), 6–3 to win the men's singles tennis title at the 2003 US Open. It was his first major title. Roddick remains the most recent American to win a major men's singles title. Roddick saved a match point en route to the title, in the semifinals against David Nalbandian. He also completed the "Summer Slam," having won Masters titles in Canada and Cincinnati in the lead-up to the US Open.
Defending champion Andre Agassi won the men's singles tennis title at the 1996 Miami Open, after Goran Ivanišević was forced to retire from the final with the score at 3–0 to Agassi in the first set. The start of the final had already been delayed for 45 minutes while Ivanišević received treatment. Ivanišević had slept awkwardly the night before the final and had woken up that morning with a very stiff neck.
Pete Sampras defeated Thomas Muster in the final, 6–3, 6–4 to win the singles tennis title at the 1997 Cincinnati Masters.
Marcelo Ríos defeated Andre Agassi in the final, 7–5, 6–3, 6–4 to win the men's singles tennis title at the 1998 Miami Open. With the win, he completed the Sunshine Double.
Pete Sampras defeated Gustavo Kuerten in the final, 6–1, 6–7(2–7), 7–6(7–5), 7–6(10–8) to win the men's singles tennis title at the 2000 Miami Open.
Thomas Enqvist defeated Tim Henman in the final, 7–6(7–5), 6–4 to win the singles tennis title at the 2000 Cincinnati Masters.
Andre Agassi defeated Pete Sampras in the final, 7–6(7–5), 7–5, 6–1 to win the men's singles tennis title at the 2001 Indian Wells Masters.
Andre Agassi defeated Jan-Michael Gambill in the final, 7–6(7–4), 6–1, 6–0 to win the men's singles tennis title at the 2001 Miami Open. With the win, he completed the Sunshine Double.
Defending champion Andre Agassi defeated Roger Federer in the final, 6–3, 6–3, 3–6, 6–4 to win the men's singles tennis title at the 2002 Miami Open.
Carlos Moyá defeated Lleyton Hewitt in the final, 7–5, 7–6(7–5) to win the singles tennis title at the 2002 Cincinnati Masters.
Pete Sampras was the defending champion, but chose not to participate that year.
Thomas Enqvist was the defending champion, but lost in the semifinals to Andre Agassi.
Andre Agassi was the defending champion but lost in the final 6–2, 6–3 against Pete Sampras.
Todd Martin was the defending champion but lost in the final 6–4, 7–6(7–2) against Pete Sampras.
Pete Sampras was the defending champion but did not compete that year.
Pete Sampras was the two-time defending champion, but lost in the final to Andre Agassi, 2–6, 4–6.
Pete Sampras was the defending champion, but did not participate.