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First round | Second round | Third round | Quarterfinals | ||||||||||||||||||||||||
1 | ![]() | 77 | 5 | 6 | |||||||||||||||||||||||
![]() | 61 | 7 | 4 | 1 | ![]() | 6 | 6 | ||||||||||||||||||||
Q | ![]() | 2 | 1 | ![]() | 1 | 2 | |||||||||||||||||||||
![]() | 6 | 6 | 1 | ![]() | 5 | 1 | |||||||||||||||||||||
![]() | 3 | 6 | 4 | 16 | ![]() | 7 | 6 | ||||||||||||||||||||
![]() | 6 | 2 | 6 | ![]() | 3 | 3 | |||||||||||||||||||||
![]() | 4 | 3 | 16 | ![]() | 6 | 6 | |||||||||||||||||||||
16 | ![]() | 6 | 6 | 16 | ![]() | 3 | 6 | 7 | |||||||||||||||||||
10 | ![]() | 6 | 6 | 10 | ![]() | 6 | 4 | 5 | |||||||||||||||||||
![]() | 3 | 2 | 10 | ![]() | 7 | 6 | |||||||||||||||||||||
![]() | 65 | 77 | 4 | ![]() | 5 | 3 | |||||||||||||||||||||
![]() | 77 | 64 | 6 | 10 | ![]() | 4 | 77 | 6 | |||||||||||||||||||
![]() | 6 | 7 | 7 | ![]() | 6 | 65 | 3 | ||||||||||||||||||||
![]() | 3 | 5 | ![]() | 5 | 5 | ||||||||||||||||||||||
![]() | 5 | 3 | 7 | ![]() | 7 | 7 | |||||||||||||||||||||
7 | ![]() | 7 | 6 |
First round | Second round | Third round | Quarterfinals | ||||||||||||||||||||||||
3 | ![]() | 6 | 77 | ||||||||||||||||||||||||
WC | ![]() | 1 | 62 | 3 | ![]() | 6 | 6 | ||||||||||||||||||||
Q | ![]() | 6 | 1 | 4 | ![]() | 3 | 3 | ||||||||||||||||||||
![]() | 1 | 6 | 6 | 3 | ![]() | 77 | 1 | 6 | |||||||||||||||||||
![]() | 62 | 63 | ![]() | 61 | 6 | 1 | |||||||||||||||||||||
![]() | 77 | 77 | ![]() | 4 | 6 | 6 | |||||||||||||||||||||
![]() | 3 | 6 | 77 | ![]() | 6 | 3 | 3 | ||||||||||||||||||||
13 | ![]() | 6 | 2 | 64 | 3 | ![]() | 5 | 77 | 7 | ||||||||||||||||||
LL | ![]() | 6 | 6 | LL | ![]() | 7 | 64 | 5 | |||||||||||||||||||
Q | ![]() | 0 | 3 | LL | ![]() | 64 | 77 | 6 | |||||||||||||||||||
![]() | 1 | 6 | 6 | ![]() | 77 | 64 | 3 | ||||||||||||||||||||
WC | ![]() | 6 | 2 | 3 | LL | ![]() | 6 | 7 | |||||||||||||||||||
![]() | 0 | 0 | r | 6 | ![]() | 3 | 5 | ||||||||||||||||||||
Q | ![]() | 6 | 1 | Q | ![]() | 2 | 1 | ||||||||||||||||||||
WC | ![]() | 2 | 4 | 6 | ![]() | 6 | 6 | ||||||||||||||||||||
6 | ![]() | 6 | 6 |
First round | Second round | Third round | Quarterfinals | ||||||||||||||||||||||||
5 | ![]() | 6 | 3 | 6 | |||||||||||||||||||||||
![]() | 0 | 6 | 1 | 5 | ![]() | 3 | 2 | ||||||||||||||||||||
![]() | 7 | 6 | ![]() | 6 | 6 | ||||||||||||||||||||||
![]() | 5 | 4 | ![]() | 6 | 63 | 3 | |||||||||||||||||||||
Q | ![]() | 77 | 4 | 2 | ![]() | 3 | 77 | 6 | |||||||||||||||||||
![]() | 65 | 6 | 6 | ![]() | 6 | 6 | |||||||||||||||||||||
![]() | 64 | 63 | 12 | ![]() | 3 | 3 | |||||||||||||||||||||
12 | ![]() | 77 | 77 | ![]() | 6 | 5 | 1 | ||||||||||||||||||||
14 | ![]() | 6 | 6 | 4 | ![]() | 4 | 7 | 6 | |||||||||||||||||||
![]() | 3 | 4 | 14 | ![]() | 6 | 6 | |||||||||||||||||||||
LL | ![]() | 6 | 4 | 5 | ![]() | 1 | 2 | ||||||||||||||||||||
![]() | 4 | 6 | 7 | 14 | ![]() | 1 | 64 | ||||||||||||||||||||
![]() | 1 | 4 | 4 | ![]() | 6 | 77 | |||||||||||||||||||||
Q | ![]() | 6 | 6 | Q | ![]() | 2 | 3 | ||||||||||||||||||||
![]() | 5 | 0 | 4 | ![]() | 6 | 6 | |||||||||||||||||||||
4 | ![]() | 7 | 6 |
First round | Second round | Third round | Quarterfinals | ||||||||||||||||||||||||
8 | ![]() | 2 | 7 | 3 | |||||||||||||||||||||||
Q | ![]() | 6 | 5 | 6 | Q | ![]() | 6 | 6 | |||||||||||||||||||
![]() | 4 | 6 | 6 | ![]() | 3 | 0 | |||||||||||||||||||||
![]() | 6 | 4 | 4 | Q | ![]() | 7 | 6 | ||||||||||||||||||||
![]() | 1 | 6 | 5 | WC | ![]() | 5 | 3 | ||||||||||||||||||||
WC | ![]() | 6 | 4 | 7 | WC | ![]() | 1 | 6 | 6 | ||||||||||||||||||
![]() | 77 | 4 | 6 | ![]() | 6 | 2 | 3 | ||||||||||||||||||||
9 | ![]() | 62 | 6 | 1 | Q | ![]() | 2 | 4 | |||||||||||||||||||
15 | ![]() | 6 | 15 | ![]() | 6 | 6 | |||||||||||||||||||||
![]() | 1 | r | 15 | ![]() | 6 | 4 | 7 | ||||||||||||||||||||
WC | ![]() | 0 | 1 | ![]() | 2 | 6 | 5 | ||||||||||||||||||||
![]() | 6 | 6 | 15 | ![]() | 6 | 6 | |||||||||||||||||||||
Q | ![]() | 6 | 6 | Q | ![]() | 2 | 3 | ||||||||||||||||||||
![]() | 1 | 2 | Q | ![]() | 6 | 6 | |||||||||||||||||||||
![]() | 6 | 2 | 62 | 2 | ![]() | 3 | 1 | ||||||||||||||||||||
2 | ![]() | 3 | 6 | 77 |
Andre Agassi defeated Andriy Medvedev in the final, 1–6, 2–6, 6–4, 6–3, 6–4 to win the men's singles tennis title at the 1999 French Open. With the win, Agassi became the second man, after Rod Laver, to complete a career Grand Slam in the Open Era. He also achieved a career Super Slam, the only men's singles player to do so.
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. With the win, he returned to the world No. 1 singles ranking, and helped end Pete Sampras' streak of six year-end No. 1 rankings.
Carlos Moyá defeated Àlex Corretja in the final, 6–3, 7–5, 6–3 to win the men's singles tennis title at the 1998 French Open.
Petr Korda defeated Marcelo Ríos in the final, 6–2, 6–2, 6–2 to win the men's singles tennis title at the 1998 Australian Open. It was Korda's only major title, and Ríos' only major final.
Patrick Rafter defeated Greg Rusedski in the final, 6–3, 6–2, 4–6, 7–5 to win the men's singles tennis title at the 1997 US Open. It was his maiden major title. Rafter became the first Australian to win the title since John Newcombe in 1973. It was Rusedski's first major final.
Pete Sampras defeated Thomas Muster in the final, 6–3, 6–4 to win the singles tennis title at the 1997 Cincinnati Masters.
Petr Korda defeated Richard Krajicek in the final, 7–6(8–6), 6–2, 6–4 to win the singles tennis title at the 1997 Eurocard Open.
Pete Sampras defeated Jonas Björkman in the final, 6–3, 4–6, 6–3, 6–1 to win the singles tennis title at the 1997 Paris Open.
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.
Marcelo Ríos won the men's singles tennis title at the 1998 Italian Open after Álbert Costa withdrew from the final.
Richard Krajicek defeated Sébastien Grosjean in the final, 4–6, 6–1, 6–2, 7–5 to win the men's singles tennis title at the 1999 Miami Open.
Marcelo Ríos defeated Mariano Zabaleta in the final, 6–7(5–7), 7–5, 5–7, 7–6(7–5), 6–2 to win the singles tennis title at the 1999 Hamburg European Open.
Pete Sampras defeated the defending champion Patrick Rafter in a rematch of the previous year's final, 7–6(9–7), 6–3 to win the singles tennis title at the 1999 Cincinnati Masters.
Álex Corretja defeated Thomas Enqvist in the final, 6–4, 6–4, 6–3 to win the men's singles tennis title at the 2000 Indian Wells Masters.
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.
Magnus Norman defeated the defending champion Gustavo Kuerten in the final, 6–3, 4–6, 6–4, 6–4 to win the men's singles tennis title at the 2000 Italian Open.
Gustavo Kuerten defeated Marat Safin in the final, 6–4, 5–7, 6–4, 5–7, 7–6(7–3) to win the singles tennis title at the 2000 Hamburg European Open.
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.
Gustavo Kuerten defeated Patrick Rafter in the final, 6–1, 6–3 to win the singles tennis title at the 2001 Cincinnati Masters.
Àlex Corretja was the defending champion, but did not participate.