Masters · 1999-08-02 · draw of 56
Canada Masters 1999
HardFinal
| 🇸🇪 Thomas Johansson | d. | 🇷🇺 Yevgeny Kafelnikov | 1-6 6-3 6-3 | H2H |
Semifinals
| 🇷🇺 Yevgeny Kafelnikov | d. | 🇺🇸 Andre Agassi | 6-1 6-4 | H2H |
| 🇸🇪 Thomas Johansson | d. | 🇩🇪 Nicolas Kiefer | 4-6 6-1 6-3 | H2H |
Quarterfinals
| 🇺🇸 Andre Agassi | d. | 🇫🇷 Fabrice Santoro | 6-0 6-3 | H2H |
| 🇷🇺 Yevgeny Kafelnikov | d. | 🇺🇸 Todd Martin | 7-6(8) 6-7(3) 6-4 | H2H |
| 🇸🇪 Thomas Johansson | d. | 🇺🇸 Jim Courier | 6-4 6-4 | H2H |
| 🇩🇪 Nicolas Kiefer | d. | 🇦🇺 Patrick Rafter | 6-3 6-7(5) 7-6(4) | H2H |
Round of 16
| 🇺🇸 Andre Agassi | d. | 🇺🇸 Michael Chang | 6-2 7-5 | H2H |
| 🇫🇷 Fabrice Santoro | d. | 🇵🇾 Ramon Delgado | 6-4 6-2 | H2H |
| 🇷🇺 Yevgeny Kafelnikov | d. | 🇿🇼 Kevin Ullyett | 6-4 7-6(5) | H2H |
| 🇺🇸 Todd Martin | d. | 🇺🇸 Vincent Spadea | 6-3 7-6(3) | H2H |
| 🇸🇪 Thomas Johansson | d. | 🇨🇦 Sebastien Lareau | 7-6(4) 4-6 6-4 | H2H |
| 🇺🇸 Jim Courier | d. | 🇿🇦 Wayne Ferreira | 6-7(3) 6-4 7-5 | H2H |
| 🇩🇪 Nicolas Kiefer | d. | 🇩🇪 Tommy Haas | 6-3 7-6(4) | H2H |
| 🇦🇺 Patrick Rafter | d. | 🇨🇿 Jiri Novak | 6-3 6-4 | H2H |
Round of 32
| 🇺🇸 Andre Agassi | d. | 🇺🇸 Richey Reneberg | 6-7(5) 6-0 6-3 | H2H |
| 🇺🇸 Michael Chang | d. | 🇫🇷 Sebastien Grosjean | 6-4 6-3 | H2H |
| 🇵🇾 Ramon Delgado | d. | 🇫🇷 Arnaud Clement | 6-3 7-6(2) | H2H |
| 🇫🇷 Fabrice Santoro | d. | 🇩🇪 Axel Pretzsch | 6-4 6-4 | H2H |
| 🇷🇺 Yevgeny Kafelnikov | d. | 🇨🇦 Daniel Nestor | 6-4 6-4 | H2H |
| 🇿🇼 Kevin Ullyett | d. | 🇿🇼 Byron Black | 5-7 6-4 7-6(6) | H2H |
| 🇺🇸 Vincent Spadea | d. | 🇳🇱 Jan Siemerink | 6-2 6-2 | H2H |
| 🇺🇸 Todd Martin | d. | 🇮🇹 Laurence Tieleman | 5-7 6-3 6-4 | H2H |
| 🇨🇦 Sebastien Lareau | d. | 🇳🇱 Richard Krajicek | 4-6 7-6(4) 6-4 | H2H |
| 🇸🇪 Thomas Johansson | d. | 🇧🇾 Max Mirnyi | 7-5 7-6(6) | H2H |
| 🇿🇦 Wayne Ferreira | d. | 🇺🇸 Jan-Michael Gambill | 7-5 3-6 7-6(8) | H2H |
| 🇺🇸 Jim Courier | d. | 🇬🇧 Tim Henman | 6-1 6-7(3) 6-4 | H2H |
| 🇩🇪 Tommy Haas | d. | 🇦🇺 Andrew Ilie | 6-3 6-4 | H2H |
| 🇩🇪 Nicolas Kiefer | d. | 🇫🇷 Guillaume Raoux | 6-4 6-0 | H2H |
| 🇨🇿 Jiri Novak | d. | 🇦🇺 Jason Stoltenberg | 3-6 6-1 7-6(5) | H2H |
| 🇦🇺 Patrick Rafter | d. | 🇺🇸 Alex O'Brien | 6-0 6-2 | H2H |