| Singles | |
|---|---|
| 1999 CA-TennisTrophy | |
| Champion |  Greg Rusedski |
| Runner-up |  Nicolas Kiefer |
| Final score | 6–7(5–7), 2–6, 6–3, 7–5, 6–4 |
| Draw | 32 |
| Seeds | 8 |
Pete Sampras was the defending champion but did not compete that year.
Greg Rusedski won in the final 6–7(5–7), 2–6, 6–3, 7–5, 6–4 against Nicolas Kiefer.
Yevgeny Kafelnikov (quarterfinals)
Todd Martin (first round)
Gustavo Kuerten (first round) Tim Henman (first round) Greg Rusedski (champion)
Richard Krajicek (semifinals) Nicolas Kiefer (final)
Nicolás Lapentti (second round)| Semifinals | Final | ||||||||||||||
| 7 | Nicolas Kiefer | 711 | 6 | ||||||||||||
| 6 | Richard Krajicek | 69 | 4 | ||||||||||||
| 7 | Nicolas Kiefer | 77 | 6 | 3 | 5 | 4 | |||||||||
| 5 | Greg Rusedski | 65 | 2 | 6 | 7 | 6 | |||||||||
| 5 | Greg Rusedski | 6 | 6 | ||||||||||||
| WC |  Roger Federer | 3 | 4 | ||||||||||||
| First round | Second round | Quarterfinals | Semifinals | ||||||||||||||||||||||||
| 1 | Y Kafelnikov | 6 | 6 | ||||||||||||||||||||||||
 T Enqvist | 3 | 4 | 1 | Y Kafelnikov | w/o | ||||||||||||||||||||||
| Q |  A Clément | 7 | 65 | 66 | J Siemerink | ||||||||||||||||||||||
| J Siemerink | 5 | 77 | 78 | 1 | Y Kafelnikov | 0 | 4 | ||||||||||||||||||||
| Q | L Burgsmüller | 65 | 6 | 3 | 7 | N Kiefer | 6 | 6 | |||||||||||||||||||
| WC |  J Melzer | 77 | 2 | 6 | WC | J Melzer | 4 | 0 | |||||||||||||||||||
 M Zabaleta | 3 | 4 | 7 | N Kiefer | 6 | 6 | |||||||||||||||||||||
| 7 | N Kiefer | 6 | 6 | 7 | N Kiefer | 711 | 6 | ||||||||||||||||||||
| 3 | G Kuerten | 1 | 77 | 4 | 6 | R Krajicek | 69 | 4 | |||||||||||||||||||
 G Ivanišević | 6 | 62 | 6 | G Ivanišević | 77 | 2 | 4 | ||||||||||||||||||||
| S Koubek | 6 | 6 | S Koubek | 63 | 6 | 6 | |||||||||||||||||||||
| Q | J Tarango | 4 | 4 | S Koubek | 2 | 1 | |||||||||||||||||||||
| M Larsson | 6 | 77 | 6 | R Krajicek | 6 | 6 | |||||||||||||||||||||
| C Pioline | 4 | 62 | M Larsson | 4 | 2 | ||||||||||||||||||||||
| Q | G Bastl | 6 | 5 | 4 | 6 | R Krajicek | 6 | 6 | |||||||||||||||||||
| 6 | R Krajicek | 4 | 7 | 6 | |||||||||||||||||||||||
| First round | Second round | Quarterfinals | Semifinals | ||||||||||||||||||||||||
| 5 | G Rusedski | 4 | 6 | 77 | |||||||||||||||||||||||
| T Johansson | 6 | 3 | 63 | 5 | G Rusedski | 4 | 7 | 6 | |||||||||||||||||||
 A Medvedev | 6 | 6 | A Medvedev | 6 | 5 | 3 | |||||||||||||||||||||
| WC | O Marach | 4 | 2 | 5 | G Rusedski | 7 | 6 | ||||||||||||||||||||
| S Grosjean | 6 | 4 | 77 | S Grosjean | 5 | 2 | |||||||||||||||||||||
| M Rosset | 3 | 6 | 65 | S Grosjean | 6 | 4 | 77 | ||||||||||||||||||||
| M Safin | 6 | 2 | 6 | M Safin | 4 | 6 | 65 | ||||||||||||||||||||
| 4 | T Henman | 4 | 6 | 3 | 5 | G Rusedski | 6 | 6 | |||||||||||||||||||
| 8 | N Lapentti | 77 | 6 | WC | R Federer | 3 | 4 | ||||||||||||||||||||
 F Clavet | 61 | 2 | 8 | N Lapentti | 2 | 3 | |||||||||||||||||||||
 K Kučera | 3 | 6 | 77 | K Kučera | 6 | 6 | |||||||||||||||||||||
| D Hrbatý | 6 | 4 | 63 | K Kučera | 6 | 4 | 1 | ||||||||||||||||||||
| WC | R Federer | 6 | 6 | WC | R Federer | 2 | 6 | 6 | |||||||||||||||||||
| V Spadea | 4 | 2 | WC | R Federer | 710 | 6 | |||||||||||||||||||||
 J Novák | 77 | 65 | 6 | J Novák | 68 | 1 | |||||||||||||||||||||
| 2 | T Martin | 63 | 77 | 4 | |||||||||||||||||||||||
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.
Three-time defending champion Pete Sampras defeated Patrick Rafter in the final, 6–7(10–12), 7–6(7–5), 6–4, 6–2 to win the gentlemen's singles tennis title at the 2000 Wimbledon Championships. It was Sampras' seventh Wimbledon title and 13th Grand Slam title overall. The win equaled William Renshaw's all-time record of Wimbledon titles, and was an Open Era record in the Gentleman's Singles until 2017, when Roger Federer won his eighth title. His victory also meant he surpassed Roy Emerson as the overall leader in men's major singles titles.
Lleyton Hewitt defeated Pete Sampras in the final, 7–6(7–4), 6–1, 6–1 to win the men's singles tennis title at the 2001 US Open. It was his first major title.
Marc Rosset was the defending champion at the Milan Indoor tennis tournament but lost in the second round to Greg Rusedski.
Yevgeny Kafelnikov was the defending champion, but lost in the semifinals to Tim Henman.
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.
Albert Costa won the singles tennis title at the 1998 Hamburg European Open after Àlex Corretja retired from the final, with the scoreline at 6–2, 6–0, 1–0.
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.
Thomas Enqvist defeated the defending champion Richard Krajicek in the final, 6–1, 6–4, 5–7, 7–5 to win the singles tennis title at the 1999 Eurocard Open.
Andre Agassi defeated Marat Safin in the final, 7–6(7–1), 6–2, 4–6, 6–4 to win the singles tennis title at the 1999 Paris Open.
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.
Greg Rusedski was the defending champion but lost in the second round to Scott Draper.
Nikolay Davydenko was the defending champion, but lost in the first round to Daniele Bracciali
Lleyton Hewitt was the defending champion, but did not participate.
Tommy Haas was the defending champion, but lost in the second round this year.
Mikhail Youzhny was the defending champion, but lost in the quarterfinals this year.
Richard Krajicek was the defending champion but did not participate.
Tim Henman was the defending champion, but lost in the final to Karol Kučera 6–4, 7–6(12–10), 4–6, 4–6, 7–6(7–2).
Àlex Corretja was the defending champion, but lost in the first round to Andrew Ilie.