Tour · 1989-08-14 · draw of 64
Montreal 1989
HardFinal
| 🇺🇸 Ivan Lendl | d. | 🇺🇸 John McEnroe | 6-1 6-3 | H2H |
Semifinals
| 🇺🇸 John McEnroe | d. | 🇺🇸 Jay Berger | 4-6 6-3 6-4 | H2H |
| 🇺🇸 Ivan Lendl | d. | 🇺🇸 Andre Agassi | 6-2 3-6 6-4 | H2H |
Quarterfinals
| 🇺🇸 Jay Berger | d. | 🇻🇪 Nicolas Pereira | 6-7 6-1 6-3 | H2H |
| 🇺🇸 Andre Agassi | d. | 🇨🇦 Andrew Sznajder | 6-1 6-0 | H2H |
| 🇺🇸 John McEnroe | d. | 🇦🇹 Alex Antonitsch | 7-5 2-6 6-3 | H2H |
| 🇺🇸 Ivan Lendl | d. | 🇨🇦 Grant Connell | 7-6 4-6 6-0 | H2H |
Round of 16
| 🇨🇦 Grant Connell | d. | 🇺🇸 Jonathan Canter | 6-3 5-7 7-5 | H2H |
| 🇦🇹 Alex Antonitsch | d. | 🇮🇹 Diego Nargiso | 3-6 6-3 6-3 | H2H |
| 🇺🇸 Jay Berger | d. | 🇺🇸 Sammy Giammalva Jr. | 6-3 7-5 | H2H |
| 🇨🇦 Andrew Sznajder | d. | 🇺🇸 Kevin Curren | 6-2 2-6 6-3 | H2H |
| 🇻🇪 Nicolas Pereira | d. | 🇺🇸 Tim Mayotte | 6-3 1-6 6-3 | H2H |
| 🇺🇸 Andre Agassi | d. | 🇳🇿 Kelly Evernden | 6-2 3-6 7-5 | H2H |
| 🇺🇸 John McEnroe | d. | 🇺🇸 Richey Reneberg | 6-3 7-6 | H2H |
| 🇺🇸 Ivan Lendl | d. | 🇺🇸 Jimmy Arias | 3-6 6-1 6-4 | H2H |
Round of 32
| 🇺🇸 Sammy Giammalva Jr. | d. | 🇺🇸 Chris Garner | 6-0 6-1 | H2H |
| 🇺🇸 Jonathan Canter | d. | 🇨🇦 Martin Laurendeau | 6-3 7-5 | H2H |
| 🇺🇸 Jimmy Arias | d. | 🇺🇸 Jeff Tarango | 6-2 6-2 | H2H |
| 🇺🇸 Richey Reneberg | d. | 🇦🇺 Richard Fromberg | 3-6 7-5 6-1 | H2H |
| 🇻🇪 Nicolas Pereira | d. | 🇺🇸 Todd Witsken | 6-3 6-1 | H2H |
| 🇳🇿 Kelly Evernden | d. | 🇺🇸 Leif Shiras | 6-4 0-6 6-4 | H2H |
| 🇨🇦 Andrew Sznajder | d. | 🇫🇷 Jean-Philippe Fleurian | 6-2 6-4 | H2H |
| 🇮🇹 Diego Nargiso | d. | 🇦🇷 Guillermo Perez-Roldan | 6-4 6-2 | H2H |
| 🇦🇹 Alex Antonitsch | d. | 🇫🇷 Yannick Noah | 6-3 6-7 7-6 | H2H |
| 🇨🇦 Grant Connell | d. | 🇸🇰 Miloslav Mecir Sr. | 6-2 4-6 6-4 | H2H |
| 🇺🇸 Jay Berger | d. | 🇦🇺 Simon Youl | W/O | H2H |
| 🇺🇸 Kevin Curren | d. | 🇦🇺 Carl Limberger | 6-4 7-5 | H2H |
| 🇺🇸 Tim Mayotte | d. | 🇫🇷 Philippe Pech | 6-2 7-6 | H2H |
| 🇺🇸 Andre Agassi | d. | 🇺🇸 Shelby Cannon | 6-3 3-6 6-3 | H2H |
| 🇺🇸 John McEnroe | d. | 🇺🇸 Ned Caswell | 6-2 4-6 6-3 | H2H |
| 🇺🇸 Ivan Lendl | d. | 🇺🇸 Kelly Jones | 7-6 6-1 | H2H |