| Singles | |
|---|---|
| 1999 Tennis Channel Open | |
| Champion |  Jan-Michael Gambill [1] |
| Runner-up |  Lleyton Hewitt |
| Score | 7–6(7–2), 4–6, 6–4 |
| Draw | 32 |
| Seeds | 8 |
Andre Agassi was the defending champion, but retired from his semifinals match this year.
Jan-Michael Gambill won the title, defeating Lleyton Hewitt 7–6(7–2), 4–6, 6–4 in the final.
Pete Sampras (second round) Patrick Rafter (second round) Andre Agassi (semifinals, retired)
Goran Ivanišević (quarterfinals)
Tommy Haas (first round)
Cédric Pioline (quarterfinals)
Thomas Muster (first round)
Gustavo Kuerten (first round)| Semifinals | Final [1] | ||||||||||||
| Jan-Michael Gambill | 5 | ||||||||||||
| 3 | Andre Agassi | 4r | |||||||||||
| Jan-Michael Gambill | 77 | 4 | 6 | ||||||||||
| Q | Lleyton Hewitt | 62 | 6 | 4 | |||||||||
| Mark Woodforde | 2 | 2 | |||||||||||
| Q | Lleyton Hewitt | 6 | 6 | ||||||||||
| First round | Second round | Quarterfinals | Semifinals | ||||||||||||||||||||||||
| 1 | P Sampras | 77 | 6 | ||||||||||||||||||||||||
 R Delgado | 62 | 2 | 1 | P Sampras | 6 | 3 | 4 | ||||||||||||||||||||
 F Squillari | 6 | 3 | 4 | J-M Gambill | 4 | 6 | 6 | ||||||||||||||||||||
| J-M Gambill | 3 | 6 | 6 | J-M Gambill | 4 | 6 | 6 | ||||||||||||||||||||
| J Stoltenberg | 63 | 5 | WC | J Gimelstob | 6 | 4 | 1 | ||||||||||||||||||||
 F Vicente | 77 | 7 | F Vicente | 65 | 2 | ||||||||||||||||||||||
| WC | J Gimelstob | 6 | 7 | WC | J Gimelstob | 77 | 6 | ||||||||||||||||||||
| 7 | T Muster | 4 | 5 | J-M Gambill | 5 | ||||||||||||||||||||||
| 3 | A Agassi | 3 | 7 | 6 | 3 | A Agassi | 4r | ||||||||||||||||||||
| F Meligeni | 6 | 5 | 3 | 3 | A Agassi | 6 | 6 | ||||||||||||||||||||
| M Zabaleta | 5 | 6 | 6 | M Zabaleta | 2 | 0 | |||||||||||||||||||||
 S Doseděl | 7 | 2 | 2 | 3 | A Agassi | 6 | 6 | ||||||||||||||||||||
| WC | C Woodruff | 3 | 6 | 67 | 6 | C Pioline | 4 | 1 | |||||||||||||||||||
| A Ilie | 6 | 2 | 79 | A Ilie | 1 | 2 | |||||||||||||||||||||
| M Puerta | 66 | 2 | 6 | C Pioline | 6 | 6 | |||||||||||||||||||||
| 6 | C Pioline | 78 | 6 | ||||||||||||||||||||||||
| First round | Second round | Quarterfinals | Semifinals | ||||||||||||||||||||||||
| 5 | T Haas | 3 | 7 | 2 | |||||||||||||||||||||||
| M Woodforde | 6 | 5 | 6 | M Woodforde | 6 | 3 | 6 | ||||||||||||||||||||
| F Clavet | 65 | 6 | 6 | F Clavet | 3 | 6 | 1 | ||||||||||||||||||||
| N Escudé | 77 | 1 | 2 | M Woodforde | 78 | 4 | 6 | ||||||||||||||||||||
| Q | H Gumy | 3 | 7 | 6 | WC/4 | G Ivanišević | 66 | 6 | 1 | ||||||||||||||||||
 S Schalken | 6 | 5 | 1 | Q | H Gumy | 4 | 4 | ||||||||||||||||||||
| S Draper | 3 | 6 | 3 | WC/4 | G Ivanišević | 6 | 6 | ||||||||||||||||||||
| WC/4 | G Ivanišević | 6 | 3 | 6 | M Woodforde | 2 | 2 | ||||||||||||||||||||
| 8 | G Kuerten | 3 | 6 | 3 | Q | L Hewitt | 6 | 6 | |||||||||||||||||||
| J Golmard | 6 | 3 | 6 | J Golmard | 3 | ||||||||||||||||||||||
| Q |  N Lapentti | 6 | 4 | 6 | Q | N Lapentti | 5r | ||||||||||||||||||||
 A Pavel | 3 | 6 | 1 | J Golmard | 1 | 0r | |||||||||||||||||||||
| Q | L Hewitt | 6 | 7 | Q | L Hewitt | 6 | 3 | ||||||||||||||||||||
 M Norman | 3 | 5 | Q | L Hewitt | 77 | 6 | |||||||||||||||||||||
| Q | A O'Brien | 3 | 4 | 2 | P Rafter | 65 | 1 | ||||||||||||||||||||
| 2 | P Rafter | 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.
Defending champion Andre Agassi defeated Arnaud Clément in the final, 6–4, 6–2, 6–2 to win the men's singles tennis title at the 2001 Australian Open. It was his third Australian Open title and seventh major title overall.
Jim Courier defeated Andre Agassi in the final, 3–6, 6–4, 2–6, 6–1, 6–4 to win the men's singles tennis title at the 1991 French Open. It was his first major singles title.
Boris Becker defeated Michael Chang in the final, 6–2, 6–4, 2–6, 6–2 to win the men's singles tennis title at the 1996 Australian Open. It was his second Australian Open title and sixth and last major title overall.
Michael Stich defeated Boris Becker in the final, 6–4, 7–6(7–4), 6–4 to win the gentlemen's singles tennis title at the 1991 Wimbledon Championships. It was his first and only major singles title.
Andre Agassi defeated Marc Rosset in the final, 6–3, 6–3, 4–6, 7–5 to win the singles tennis title at the 1994 Paris Open.
Defending champion Pete Sampras defeated Andre Agassi in the final, 7–5, 6–3, 7–5 to win the men's singles tennis title at the 1995 Indian Wells Masters.
Andre Agassi defeated the two-time defending champion Michael Chang in the final, 7–5, 6–2 to win the singles tennis title at the 1995 Cincinnati Masters.
Defending champion Andre Agassi defeated Michael Chang in a rematch of the previous year's final, 7–6(7–4), 6–4 to win the singles tennis title at the 1996 Cincinnati Masters.
Marat Safin defeated Mark Philippoussis in the final, 3–6, 7–6(9–7), 6–4, 3–6, 7–6(10–8) to win the singles tennis title at the 2000 Paris Masters. With the win, Safin became the world No. 1 for the first time.
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.
Stefan Edberg defeated Andre Agassi in the final, 6–4, 5–7, 7–6(7–1), 7–6(8–6) to win the men's singles tennis title at the 1990 Indian Wells Masters.
Goran Ivanišević was the defending champion but lost in the semifinals to Andre Agassi.
Michael Chang was the defending champion but lost in the second round to Pete Sampras.
Andre Agassi was the defending champion and won in the final 6–2, 6–4 against Jan-Michael Gambill.
Thomas Enqvist was the defending champion but lost in the quarterfinals to Todd Martin.
Mikael Pernfors was the defending champion but did not participate that year.
Mardy Fish was the defending champion, but did not participate this year.
Andre Agassi was the defending champion, but lost in the quarterfinals this year.