| Singles | |
|---|---|
| 1999 Stella Artois Championships | |
| Champion |  Pete Sampras |
| Runner-up |  Tim Henman |
| Score | 6–7(1–7), 6–4, 7–6(7–4) |
| Draw | 56 |
| Seeds | 16 |
Scott Draper was the defending champion but lost in the third round to Sargis Sargsian.
Pete Sampras won in the final 6–7(1–7), 6–4, 7–6(7–4) against Tim Henman.
This was the only year in which Roger Federer competed in this tournament.
The top eight seeds received a bye to the second round.
Yevgeny Kafelnikov (second round) Pete Sampras (champion) Tim Henman (final)
Mark Philippoussis (third round) Todd Martin (third round)
Karol Kučera (quarterfinals) Greg Rusedski (quarterfinals)
Goran Ivanišević (quarterfinals)
Thomas Enqvist (first round)
Wayne Ferriera (third round)
Cédric Pioline (quarterfinals) Jason Stoltenberg (third round)
Byron Black (third round) Lleyton Hewitt (semifinals) Scott Draper (third round) Fabrice Santoro (first round)| Semifinals | Final | ||||||||||||
 Sargis Sargsian | 1 | 3 | |||||||||||
| 3 | Tim Henman | 6 | 6 | ||||||||||
| 3 | Tim Henman | 77 | 4 | 64 | |||||||||
| WC/2 | Pete Sampras | 61 | 6 | 77 | |||||||||
| 14 | Lleyton Hewitt | 6 | 4 | 64 | |||||||||
| WC/2 | Pete Sampras | 4 | 6 | 77 | |||||||||
| First round | Second round | Third round | Quarterfinals | ||||||||||||||||||||||||
| 1 | Y Kafelnikov | 6 | 3 | 3 | |||||||||||||||||||||||
| S Sargsian | 6 | 6 | S Sargsian | 3 | 6 | 6 | |||||||||||||||||||||
 M Damm | 3 | 1 | S Sargsian | 6 | 6 | ||||||||||||||||||||||
| P Korda | 4 | 4 | 15 | S Draper | 3 | 2 | |||||||||||||||||||||
 B Becker | 6 | 6 | B Becker | 63 | 3 | ||||||||||||||||||||||
| Q | O Motevassel | 63 | 67 | 15 | S Draper | 77 | 6 | ||||||||||||||||||||
| 15 | S Draper | 77 | 79 | S Sargsian | 6 | 6 | |||||||||||||||||||||
| 10 | W Ferreira | 3 | 7 | 6 | 7 | G Rusedski | 2 | 4 | |||||||||||||||||||
 L Tieleman | 6 | 5 | 1 | 10 | W Ferreira | 65 | 6 | 6 | |||||||||||||||||||
| A Dupuis | 5 | 1 | J Tarango | 77 | 4 | 2 | |||||||||||||||||||||
| J Tarango | 7 | 6 | 10 | W Ferreira | 5 | 6 | 3 | ||||||||||||||||||||
| P Goldstein | 6 | 7 | 7 | G Rusedski | 7 | 4 | 6 | ||||||||||||||||||||
| Q |  G Motomura | 3 | 5 | P Goldstein | 3 | 4 | |||||||||||||||||||||
| 7 | G Rusedski | 6 | 6 | ||||||||||||||||||||||||
| First round | Second round | Third round | Quarterfinals | ||||||||||||||||||||||||
| 3 | T Henman | 6 | 78 | ||||||||||||||||||||||||
 C Mamiit | 6 | 6 | C Mamiit | 3 | 66 | ||||||||||||||||||||||
| A Pretzsch | 3 | 4 | 3 | T Henman | 6 | 6 | |||||||||||||||||||||
| A Clément | 4 | 13 | B Black | 1 | 4 | ||||||||||||||||||||||
| N Escudé | 0r | A Clément | 4 | 3 | |||||||||||||||||||||||
 R Federer | 3 | 0 | 13 | B Black | 6 | 6 | |||||||||||||||||||||
| 13 | B Black | 6 | 6 | 3 | T Henman | 6 | 66 | 77 | |||||||||||||||||||
| 12 | J Stoltenberg | 6 | 6 | 6 | K Kučera | 1 | 78 | 65 | |||||||||||||||||||
| W Black | 3 | 4 | 12 | J Stoltenberg | 77 | 6 | |||||||||||||||||||||
| M Tillström | 79 | 64 | 4 | Q | M Lee | 61 | 1 | ||||||||||||||||||||
| Q | M Lee | 67 | 77 | 6 | 12 | J Stoltenberg | 3 | 3 | |||||||||||||||||||
 K Carlsen | 2 | 6 | 1 | 6 | K Kučera | 6 | 6 | ||||||||||||||||||||
| WC | J Courier | 6 | 4 | 6 | WC | J Courier | 6 | 4 | 1 | ||||||||||||||||||
| 6 | K Kučera | 3 | 6 | 6 | |||||||||||||||||||||||
| First round | Second round | Third round | Quarterfinals | ||||||||||||||||||||||||
| 6 | T Martin | 78 | 77 | ||||||||||||||||||||||||
| R Fromberg | 7 | 74 | R Fromberg | 66 | 64 | ||||||||||||||||||||||
| WC | M Norman | 5 | 64 | 6 | T Martin | 6 | 3 | 5 | |||||||||||||||||||
 D van Scheppingen | 6 | 2 | 4 | 11 | C Pioline | 1 | 6 | 7 | |||||||||||||||||||
| M Woodforde | 3 | 6 | 6 | M Woodforde | 4 | 5 | |||||||||||||||||||||
| M Navarra | 62 | 6 | 1 | 11 | C Pioline | 6 | 7 | ||||||||||||||||||||
| 11 | C Pioline | 77 | 3 | 6 | 11 | C Pioline | 5 | 4 | |||||||||||||||||||
| 14 | L Hewitt | 77 | 3 | 6 | 14 | L Hewitt | 7 | 6 | |||||||||||||||||||
| D Nargiso | 62 | 6 | 2 | 14 | L Hewitt | 6 | 6 | ||||||||||||||||||||
| WC | C Wilkinson | 4 | 77 | 6 | WC | C Wilkinson | 4 | 3 | |||||||||||||||||||
| T Suzuki | 6 | 65 | 1 | 14 | L Hewitt | 64 | 6 | 6 | |||||||||||||||||||
| J-M Gambill | 6 | 6 | 4 | M Philippoussis | 77 | 3 | 2 | ||||||||||||||||||||
| Q | M Sell | 4 | 2 | J-M Gambill | 6 | 3 | 4 | ||||||||||||||||||||
| 4 | M Philippoussis | 2 | 6 | 6 | |||||||||||||||||||||||
| First round | Second round | Third round | Quarterfinals | ||||||||||||||||||||||||
| 8 | G Ivanišević | 6 | 6 | ||||||||||||||||||||||||
 O Stanoytchev | 4 | 6 | 6 | O Stanoytchev | 4 | 4 | |||||||||||||||||||||
| P Wessels | 6 | 2 | 4 | 8 | G Ivanišević | 6 | 63 | 6 | |||||||||||||||||||
 S Lareau | 6 | 6 | S Lareau | 4 | 77 | 4 | |||||||||||||||||||||
| WC | B Cowan | 4 | 2 | S Lareau | 6 | 4 | 6 | ||||||||||||||||||||
| M Kohlmann | 6 | 6 | M Kohlmann | 1 | 6 | 4 | |||||||||||||||||||||
| 9 | T Enqvist | 4 | 4 | 8 | G Ivanišević | 5 | 4 | ||||||||||||||||||||
| 16 | F Santoro | 3 | 66 | WC/2 | P Sampras | 7 | 6 | ||||||||||||||||||||
| Q | P Tramacchi | 6 | 78 | Q | P Tramacchi | 3 | 4 | ||||||||||||||||||||
| Q | W Arthurs | 7 | 6 | Q | W Arthurs | 6 | 6 | ||||||||||||||||||||
| Q | A Parmar | 5 | 2 | Q | W Arthurs | 5 | 3 | ||||||||||||||||||||
| R Wassen | 2 | 1 | WC/2 | P Sampras | 7 | 6 | |||||||||||||||||||||
| T Woodbridge | 6 | 6 | T Woodbridge | 4 | 78 | 4 | |||||||||||||||||||||
| WC/2 | P Sampras | 6 | 66 | 6 | |||||||||||||||||||||||
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.
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.
Pete Sampras defeated Cédric Pioline in the final, 6–4, 6–2, 6–4 to win the gentlemen's singles tennis title at the 1997 Wimbledon Championships. It was his fourth Wimbledon title.
Defending champion Pete Sampras defeated Goran Ivanišević in the final, 6–7(2–7), 7–6(11–9), 6–4, 3–6, 6–2 to win the gentlemen's singles tennis title at the 1998 Wimbledon Championships. With the win, Sampras equalled Björn Borg's Open Era record of five Wimbledon titles.
Mark Philippoussis was the defending champion but lost in the first round to Jordi Burillo.
Pete Sampras was the defending champion but lost in the final 6–4, 6–4 against Lleyton Hewitt.
Guillermo Cañas defeated Andy Roddick in the final, 6–4, 7–5 to win the men's singles tennis title at the 2002 Canada Masters.
Tommy Haas was the defending champion but did not compete that year.
Pete Sampras defeated Thomas Muster in the final, 6–3, 6–4 to win the singles tennis title at the 1997 Cincinnati Masters.
Patrick Rafter defeated Richard Krajicek in the final, 7–6,(7–3), 6–4 to win the men's singles tennis title at the 1998 Canadian Open.
Patrick Rafter defeated the defending champion Pete Sampras in the final, 1–6, 7–6(7–2), 6–4 to win the singles tennis title at the 1998 Cincinnati Masters.
Greg Rusedski defeated the defending champion Pete Sampras in the final, 6–4, 7–6(7–4), 6–3 to win the singles tennis title at the 1998 Paris Open.
Mark Philippoussis defeated Carlos Moyá in the final, 5–7, 6–4, 6–4, 4–6, 6–2 to win the men's singles tennis title at the 1999 Indian Wells Masters.
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.
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.
Goran Ivanišević was the defending champion but did not compete that year.
Lleyton Hewitt was the defending champion and won in the final 7–6(7–3), 7–6(7–3) against Tim Henman.
The 1996 Japan Open Tennis Championships included this tournament in men's singles. Jim Courier was the defending champion but did not compete that year.
Thomas Enqvist was the defending champion but lost in the quarterfinals to Todd Martin.