Tour · 1989-07-31 · draw of 64
Stratton Mountain 1989
HardFinal
| 🇺🇸 Brad Gilbert | d. | 🇺🇸 Jim Pugh | 7-5 6-0 | H2H |
Semifinals
| 🇺🇸 Jim Pugh | d. | 🇺🇸 Jim Grabb | 6-2 6-4 | H2H |
| 🇺🇸 Brad Gilbert | d. | 🇺🇸 David Wheaton | 5-7 7-6 6-4 | H2H |
Quarterfinals
| 🇺🇸 Jim Pugh | d. | 🇺🇸 Robert Seguso | 6-3 6-2 | H2H |
| 🇺🇸 David Wheaton | d. | 🇺🇸 Jim Courier | 6-4 6-2 | H2H |
| 🇺🇸 Brad Gilbert | d. | 🇺🇸 Glenn Layendecker | 6-4 7-5 | H2H |
| 🇺🇸 Jim Grabb | d. | 🇺🇸 Michael Chang | 6-2 6-4 | H2H |
Round of 16
| 🇺🇸 Glenn Layendecker | d. | 🇨🇦 Grant Connell | 7-5 6-2 | H2H |
| 🇺🇸 Jim Pugh | d. | 🇺🇸 Jared Palmer | 3-6 7-6 6-3 | H2H |
| 🇺🇸 Robert Seguso | d. | 🇨🇦 Andrew Sznajder | 6-3 3-6 6-2 | H2H |
| 🇺🇸 Jim Grabb | d. | 🇺🇸 Johan Kriek | 6-3 6-4 | H2H |
| 🇺🇸 Jim Courier | d. | 🇺🇸 Dan Goldie | 6-2 6-3 | H2H |
| 🇺🇸 Brad Gilbert | d. | 🇦🇺 Wally Masur | 6-4 7-6 | H2H |
| 🇺🇸 Michael Chang | d. | 🇺🇸 Derrick Rostagno | 6-3 6-2 | H2H |
| 🇺🇸 David Wheaton | d. | 🇺🇸 Andre Agassi | 1-6 7-6 6-1 | H2H |
Round of 32
| 🇦🇺 Wally Masur | d. | 🇿🇦 Pieter Aldrich | 3-6 6-3 6-4 | H2H |
| 🇺🇸 David Wheaton | d. | 🇺🇸 Scott Davis | 6-1 6-4 | H2H |
| 🇺🇸 Derrick Rostagno | d. | 🇺🇸 Tim Donovan | 7-6 7-5 | H2H |
| 🇺🇸 Jim Pugh | d. | 🇨🇦 Chris Pridham | 3-6 7-5 7-6 | H2H |
| 🇺🇸 Robert Seguso | d. | 🇺🇸 Tim Wilkison | 6-3 6-2 | H2H |
| 🇺🇸 Glenn Layendecker | d. | 🇺🇸 Paul Annacone | 6-4 7-6 | H2H |
| 🇺🇸 Johan Kriek | d. | 🇺🇸 Steve Bryan | 1-6 6-4 7-6 | H2H |
| 🇺🇸 Jim Courier | d. | 🇺🇸 Sammy Giammalva Jr. | 6-2 6-2 | H2H |
| 🇺🇸 Dan Goldie | d. | 🇺🇸 Ken Flach | 6-7 6-1 7-6 | H2H |
| 🇺🇸 Jim Grabb | d. | 🇫🇷 Yannick Noah | 6-1 6-4 | H2H |
| 🇨🇦 Andrew Sznajder | d. | 🇺🇸 Jay Berger | 6-2 2-6 6-3 | H2H |
| 🇨🇦 Grant Connell | d. | 🇮🇱 Amos Mansdorf | 6-3 7-6 | H2H |
| 🇺🇸 Jared Palmer | d. | 🇺🇸 Kevin Curren | 6-4 6-3 | H2H |
| 🇺🇸 Brad Gilbert | d. | 🇮🇹 Gianluca Pozzi | 6-1 6-2 | H2H |
| 🇺🇸 Michael Chang | d. | 🇸🇪 Johan Carlsson | 7-5 6-3 | H2H |
| 🇺🇸 Andre Agassi | d. | 🇺🇸 Marty Davis | 6-1 3-6 6-3 | H2H |