Match log updated: 2026-08-31 13:51 UTC
Brad Gilbert — ATP Match Log
782 main-draw matches · 506–276 · 64.7% wins
| Opponent | Score | Result | H2H | Match Data | Date ↑ | Round | Tournament | Category | Surface |
|---|---|---|---|---|---|---|---|---|---|
| Jimmy Arias | 6-2 2-6 6-3 | W | H2H | Match data | Aug 9, 1985* | R16 | Stratton Mountain | ATP 250 | Hard |
| Ivan Lendl | 3-6 3-6 | L | H2H | Match data | Aug 10, 1985* | QF | Stratton Mountain | ATP 250 | Hard |
| Peter Doohan | 6-4 6-3 | W | H2H | Match data | Aug 15, 1985* | R32 | Cleveland | ATP 250 | Hard |
| Ricky Brown | 6-3 6-4 | W | H2H | Match data | Aug 16, 1985* | R16 | Cleveland | ATP 250 | Hard |
| Matt Doyle | 6-1 6-0 | W | — | Match data | Aug 17, 1985* | QF | Cleveland | ATP 250 | Hard |
| Bud Schultz | 6-4 6-4 | W | H2H | Match data | Aug 17, 1985* | SF | Cleveland | ATP 250 | Hard |
| Brad Drewett | 6-3 6-2 | W | H2H | Match data | Aug 18, 1985* | F | Cleveland | ATP 250 | Hard |
| Christo Van Rensburg | 6-2 6-2 6-2 | W | H2H | Match data | Aug 29, 1985* | R128 | US Open | Grand Slam | Hard |
| Luke Jensen | 6-3 6-2 6-3 | W | H2H | Match data | Aug 31, 1985* | R64 | US Open | Grand Slam | Hard |
| Stefan Edberg | 6-4 4-6 1-6 4-6 | L | H2H | Match data | Sep 2, 1985* | R32 | US Open | Grand Slam | Hard |
| Brad Drewett | 6-2 7-6 | W | H2H | Match data | Sep 12, 1985* | R32 | Stuttgart Open | ATP 250 | Clay |
| Juan Aguilera | 7-6 6-3 | W | H2H | Match data | Sep 13, 1985* | R16 | Stuttgart Open | ATP 250 | Clay |
| Andreas Maurer | 6-0 6-3 | W | H2H | Match data | Sep 14, 1985* | QF | Stuttgart Open | ATP 250 | Clay |
| Tomas Smid | 6-4 4-6 7-5 | W | H2H | Match data | Sep 14, 1985* | SF | Stuttgart Open | ATP 250 | Clay |
| Ivan Lendl | 4-6 0-6 | L | H2H | Match data | Sep 15, 1985* | F | Stuttgart Open | ATP 250 | Clay |
| Marcel Freeman | 7-6 6-2 | W | H2H | Match data | Sep 19, 1985* | R32 | Los Angeles Open | ATP 250 | Hard |
| John Lloyd | 7-5 6-3 | W | — | Match data | Sep 20, 1985* | R16 | Los Angeles Open | ATP 250 | Hard |
| John McEnroe | 6-4 0-6 3-6 | L | H2H | Match data | Sep 21, 1985* | QF | Los Angeles Open | ATP 250 | Hard |
| Terry Moor | 6-4 6-3 | W | H2H | Match data | Sep 26, 1985* | R32 | San Francisco | ATP 250 | Carpet |
| Peter Fleming | 6-2 6-2 | W | H2H | Match data | Sep 27, 1985* | R16 | San Francisco | ATP 250 | Carpet |
| Stefan Edberg | 2-6 2-6 | L | H2H | Match data | Sep 28, 1985* | QF | San Francisco | ATP 250 | Carpet |
| Bob Green | 6-2 7-6 | W | H2H | Match data | Oct 10, 1985* | R32 | South African Open | ATP 250 | Hard |
| Barry Moir | 6-3 5-7 6-3 | W | H2H | Match data | Oct 11, 1985* | R16 | South African Open | ATP 250 | Hard |
| Martin Wostenholme | 6-4 6-2 | W | H2H | Match data | Oct 12, 1985* | QF | South African Open | ATP 250 | Hard |
| Johan Kriek | 6-4 6-4 | W | H2H | Match data | Oct 12, 1985* | SF | South African Open | ATP 250 | Hard |
| Matt Anger | 4-6 6-3 3-6 2-6 | L | H2H | Match data | Oct 13, 1985* | F | South African Open | ATP 250 | Hard |
| Steve Shaw | 6-3 6-2 | W | H2H | Match data | Oct 17, 1985* | R32 | Tel Aviv | ATP 250 | Hard |
| Karsten Schulz | 6-2 6-3 | W | H2H | Match data | Oct 18, 1985* | R16 | Tel Aviv | ATP 250 | Hard |
| Gianni Ocleppo | 6-2 6-4 | W | H2H | Match data | Oct 19, 1985* | QF | Tel Aviv | ATP 250 | Hard |
| Shahar Perkiss | 6-2 6-1 | W | H2H | Match data | Oct 19, 1985* | SF | Tel Aviv | ATP 250 | Hard |
| Amos Mansdorf | 6-3 6-2 | W | H2H | Match data | Oct 20, 1985* | F | Tel Aviv | ATP 250 | Hard |
| Tsuyoshi Fukui | 7-6(5) 6-2 | W | H2H | Match data | Oct 24, 1985* | R32 | Tokyo Indoor | ATP 250 | Carpet |
| Tim Mayotte | 2-6 2-6 | L | H2H | Match data | Oct 25, 1985* | R16 | Tokyo Indoor | ATP 250 | Carpet |
| Wolfgang Popp | 6-3 6-3 | W | H2H | Match data | Nov 21, 1985* | R32 | Hong Kong Open | ATP 250 | Hard |
| Leonardo Lavalle | 5-7 4-6 | L | H2H | Match data | Nov 22, 1985* | R16 | Hong Kong Open | ATP 250 | Hard |
| Shahar Perkiss | 6-3 6-3 7-6 | W | H2H | Match data | Nov 29, 1985* | R64 | Australian Open | Grand Slam | Grass |
| Christo Steyn | 6-2 4-6 4-6 5-7 | L | H2H | Match data | Dec 1, 1985* | R32 | Australian Open | Grand Slam | Grass |
| John McEnroe | 5-7 6-4 6-1 | W | H2H | Match data | Jan 19, 1986* | R16 | ATP Finals | ATP Finals | Carpet |
| Anders Jarryd | 1-6 2-6 | L | H2H | Match data | Jan 20, 1986* | QF | ATP Finals | ATP Finals | Carpet |
| Wojtek Fibak | 6-3 6-1 | W | H2H | Match data | Jan 30, 1986* | R32 | Philadelphia | ATP 250 | Carpet |
| Anders Jarryd | 7-6 6-0 | W | H2H | Match data | Jan 31, 1986* | R16 | Philadelphia | ATP 250 | Carpet |
| Jakob Hlasek | 6-7 6-4 6-3 | W | H2H | Match data | Feb 1, 1986* | QF | Philadelphia | ATP 250 | Carpet |
| Ivan Lendl | 5-7 6-4 2-6 | L | H2H | Match data | Feb 1, 1986* | SF | Philadelphia | ATP 250 | Carpet |
| John Sadri | 7-6 6-2 | W | H2H | Match data | Feb 6, 1986* | R32 | Memphis | ATP 250 | Carpet |
| Marty Davis | 7-5 6-4 | W | H2H | Match data | Feb 7, 1986* | R16 | Memphis | ATP 250 | Carpet |
| Jimmy Connors | 3-6 6-4 6-4 | W | H2H | Match data | Feb 8, 1986* | QF | Memphis | ATP 250 | Carpet |
| Anders Jarryd | 6-3 6-0 | W | H2H | Match data | Feb 8, 1986* | SF | Memphis | ATP 250 | Carpet |
| Stefan Edberg | 7-5 7-6 | W | H2H | Match data | Feb 9, 1986* | F | Memphis | ATP 250 | Carpet |
| Diego Perez | 6-3 6-3 | W | H2H | Match data | Feb 11, 1986* | R128 | Miami Open | ATP 500 | Hard |
| Ronald Agenor | 6-2 7-5 | W | H2H | Match data | Feb 12, 1986* | R64 | Miami Open | ATP 500 | Hard |
| Thierry Tulasne | 5-7 2-6 | L | H2H | Match data | Feb 13, 1986* | R32 | Miami Open | ATP 500 | Hard |
| Greg Holmes | 2-6 4-6 | L | H2H | Match data | Mar 20, 1986* | R32 | Fort Myers | ATP 250 | Hard |
| Tim Mayotte | 6-7 7-6 3-6 | L | H2H | Match data | Mar 27, 1986* | R32 | Chicago | ATP 250 | Carpet |
| Ricardo Acuna | 6-4 6-3 | W | H2H | Match data | Apr 3, 1986* | R32 | Atlanta | ATP 250 | Carpet |
| Mel Purcell | 6-4 6-4 | W | H2H | Match data | Apr 4, 1986* | R16 | Atlanta | ATP 250 | Carpet |
| David Pate | 6-2 3-6 3-6 | L | H2H | Match data | Apr 5, 1986* | QF | Atlanta | ATP 250 | Carpet |
| Johan Kriek | 4-6 1-6 6-2 6-4 3-6 | L | H2H | Match data | Apr 11, 1986* | R16 | Dallas | ATP 250 | Carpet |
| Bud Schultz | 7-5 6-1 | W | H2H | Match data | May 7, 1986* | R64 | Forest Hills | ATP 250 | Clay |
| Leonardo Lavalle | 6-1 4-6 3-6 | L | H2H | Match data | May 8, 1986* | R32 | Forest Hills | ATP 250 | Clay |
| Mike Leach | 6-4 6-2 | W | H2H | Match data | Jun 11, 1986* | R64 | Queen's Club Championships | ATP 250 | Grass |
| Ramesh Krishnan | 5-7 1-6 | L | H2H | Match data | Jun 12, 1986* | R32 | Queen's Club Championships | ATP 250 | Grass |
| Mark Woodforde | 6-3 6-4 6-4 | W | H2H | Match data | Jun 25, 1986* | R128 | Wimbledon | Grand Slam | Grass |
| Mike Leach | 7-6 7-6 6-2 | W | H2H | Match data | Jun 27, 1986* | R64 | Wimbledon | Grand Slam | Grass |
| Milan Srejber | 7-5 6-7 6-3 6-3 | W | H2H | Match data | Jun 29, 1986* | R32 | Wimbledon | Grand Slam | Grass |
| Miloslav Mecir | 6-3 6-7 1-6 2-6 | L | H2H | Match data | Jul 2, 1986* | R16 | Wimbledon | Grand Slam | Grass |
| Bob Green | 6-3 6-3 | W | H2H | Match data | Jul 24, 1986* | R32 | Livingston | ATP 250 | Hard |
| Todd Nelson | 6-1 6-4 | W | H2H | Match data | Jul 25, 1986* | R16 | Livingston | ATP 250 | Hard |
| Sammy Giammalva Jr | 6-3 6-4 | W | — | Match data | Jul 26, 1986* | QF | Livingston | ATP 250 | Hard |
| Christo Van Rensburg | 6-3 6-4 | W | H2H | Match data | Jul 26, 1986* | SF | Livingston | ATP 250 | Hard |
| Mike Leach | 6-2 6-2 | W | H2H | Match data | Jul 27, 1986* | F | Livingston | ATP 250 | Hard |
| Sammy Giammalva Jr | 2-6 6-4 6-1 | W | — | Match data | Aug 6, 1986* | R64 | Stratton Mountain | ATP 250 | Hard |
| Marcel Freeman | 3-6 6-2 6-0 | W | H2H | Match data | Aug 7, 1986* | R32 | Stratton Mountain | ATP 250 | Hard |
| Greg Holmes | 6-2 4-6 6-2 | W | H2H | Match data | Aug 8, 1986* | R16 | Stratton Mountain | ATP 250 | Hard |
| Ivan Lendl | 2-6 6-3 2-6 | L | H2H | Match data | Aug 9, 1986* | QF | Stratton Mountain | ATP 250 | Hard |
| Glenn Layendecker | 6-0 6-4 | W | H2H | Match data | Aug 14, 1986* | R32 | Canadian Open | ATP 500 | Hard |
| Bud Schultz | 6-3 3-6 4-6 | L | H2H | Match data | Aug 16, 1986* | R16 | Canadian Open | ATP 500 | Hard |
| Tomm Warneke | 2-6 6-4 6-3 6-3 | W | H2H | Match data | Aug 28, 1986* | R128 | US Open | Grand Slam | Hard |
| Nduka Odizor | 5-7 6-2 6-4 6-2 | W | H2H | Match data | Aug 30, 1986* | R64 | US Open | Grand Slam | Hard |
| Johan Kriek | 6-2 7-5 6-2 | W | H2H | Match data | Sep 1, 1986* | R32 | US Open | Grand Slam | Hard |
| Ivan Lendl | 5-7 1-6 2-6 | L | H2H | Match data | Sep 4, 1986* | R16 | US Open | Grand Slam | Hard |
| John Sadri | 6-4 6-4 | W | H2H | Match data | Sep 18, 1986* | R32 | Los Angeles Open | ATP 250 | Hard |
| Jonathan Canter | 6-3 6-3 | W | H2H | Match data | Sep 19, 1986* | R16 | Los Angeles Open | ATP 250 | Hard |
| Pat Cash | 6-2 6-2 | W | H2H | Match data | Sep 20, 1986* | QF | Los Angeles Open | ATP 250 | Hard |
| John McEnroe | 1-6 6-3 3-6 | L | H2H | Match data | Sep 20, 1986* | SF | Los Angeles Open | ATP 250 | Hard |
| Thomas Hogstedt | 7-5 7-6 | W | H2H | Match data | Oct 9, 1986* | R32 | Tel Aviv | ATP 250 | Hard |
| Shahar Perkiss | 6-4 7-6 | W | H2H | Match data | Oct 10, 1986* | R16 | Tel Aviv | ATP 250 | Hard |
| Gilad Bloom | 6-3 1-6 7-5 | W | H2H | Match data | Oct 11, 1986* | QF | Tel Aviv | ATP 250 | Hard |
| Christo Steyn | 6-4 6-3 | W | H2H | Match data | Oct 11, 1986* | SF | Tel Aviv | ATP 250 | Hard |
| Aaron Krickstein | 7-5 6-2 | W | H2H | Match data | Oct 12, 1986* | F | Tel Aviv | ATP 250 | Hard |
| Jan Gunnarsson | 6-2 5-7 6-3 | W | H2H | Match data | Oct 16, 1986* | R32 | Swiss Indoors | ATP 250 | Hard |
| Peter Lundgren | 7-5 6-4 | W | H2H | Match data | Oct 17, 1986* | R16 | Swiss Indoors | ATP 250 | Hard |
| Gary Muller | 6-3 7-5 | W | — | Match data | Oct 18, 1986* | QF | Swiss Indoors | ATP 250 | Hard |
| Stefan Edberg | 6-7 2-6 | L | H2H | Match data | Oct 18, 1986* | SF | Swiss Indoors | ATP 250 | Hard |
| Patrik Kuhnen | 6-4 6-0 | W | H2H | Match data | Oct 23, 1986* | R32 | Vienna Open | ATP 250 | Hard |
| Peter Elter | 6-1 6-3 | W | H2H | Match data | Oct 24, 1986* | R16 | Vienna Open | ATP 250 | Hard |
| Richard Matuszewski | 4-6 6-3 7-5 | W | H2H | Match data | Oct 25, 1986* | QF | Vienna Open | ATP 250 | Hard |
| Jonas Svensson | 6-3 6-2 | W | H2H | Match data | Oct 25, 1986* | SF | Vienna Open | ATP 250 | Hard |
| Karel Novacek | 3-6 6-3 7-5 6-0 | W | H2H | Match data | Oct 26, 1986* | F | Vienna Open | ATP 250 | Hard |
| Brad Drewett | 7-5 6-3 6-2 | W | H2H | Match data | Jan 16, 1987* | R64 | Australian Open | Grand Slam | Grass |
| Derrick Rostagno | 6-4 2-6 3-6 1-6 | L | H2H | Match data | Jan 18, 1987* | R32 | Australian Open | Grand Slam | Grass |
| Broderick Dyke | 6-7 7-6 4-6 | L | H2H | Match data | Feb 5, 1987* | R32 | Philadelphia | ATP 250 | Carpet |
| John Sadri | 6-1 6-3 | W | H2H | Match data | Feb 12, 1987* | R32 | Memphis | ATP 250 | Hard |
| Eric Jelen | 6-3 6-3 | W | H2H | Match data | Feb 13, 1987* | R16 | Memphis | ATP 250 | Hard |
| Johan Kriek | 6-2 7-6 | W | H2H | Match data | Feb 14, 1987* | QF | Memphis | ATP 250 | Hard |
| Stefan Edberg | 4-6 6-7 | L | H2H | Match data | Feb 14, 1987* | SF | Memphis | ATP 250 | Hard |
| Joey Rive | 6-3 6-2 6-4 | W | H2H | Match data | Feb 24, 1987* | R128 | Miami Open | ATP 500 | Hard |
| Ronald Agenor | 6-2 6-1 6-4 | W | H2H | Match data | Feb 25, 1987* | R64 | Miami Open | ATP 500 | Hard |
| Marc Flur | 7-6 7-6 6-3 | W | H2H | Match data | Feb 26, 1987* | R32 | Miami Open | ATP 500 | Hard |
| Ivan Lendl | 2-6 2-6 4-6 | L | H2H | Match data | Feb 28, 1987* | R16 | Miami Open | ATP 500 | Hard |
| Mark Dickson | 6-1 6-4 | W | H2H | Match data | Mar 19, 1987* | R32 | Orlando | ATP 250 | Hard |
| Matt Anger | 6-1 7-6 | W | H2H | Match data | Mar 20, 1987* | R16 | Orlando | ATP 250 | Hard |
| Marcel Freeman | 4-6 6-3 6-1 | W | H2H | Match data | Mar 21, 1987* | QF | Orlando | ATP 250 | Hard |
| Jimmy Connors | 6-3 4-6 2-6 | L | H2H | Match data | Mar 21, 1987* | SF | Orlando | ATP 250 | Hard |
| Kelly Evernden | 6-3 6-2 | W | H2H | Match data | Apr 2, 1987* | R32 | Chicago | ATP 250 | Carpet |
| Bill Scanlon | 5-7 4-6 | L | H2H | Match data | Apr 3, 1987* | R16 | Chicago | ATP 250 | Carpet |
| Bruno Oresar | 1-6 7-5 2-6 6-4 6-4 | W | H2H | Match data | May 27, 1987* | R128 | Roland Garros | Grand Slam | Clay |
| Jordi Arrese | 5-7 2-6 1-6 | L | H2H | Match data | May 29, 1987* | R64 | Roland Garros | Grand Slam | Clay |
| Stuart Bale | 7-6 6-4 6-3 | W | H2H | Match data | Jun 24, 1987* | R128 | Wimbledon | Grand Slam | Grass |
| Chris Bailey | 6-2 6-2 6-4 | W | H2H | Match data | Jun 26, 1987* | R64 | Wimbledon | Grand Slam | Grass |
| Alexander Volkov | 6-7 6-0 3-6 4-6 | L | H2H | Match data | Jun 28, 1987* | R32 | Wimbledon | Grand Slam | Grass |
| Jaime Yzaga | 1-6 1-6 | L | H2H | Match data | Jul 9, 1987* | R32 | Swiss Open Gstaad | ATP 250 | Clay |
| Broderick Dyke | 6-1 6-4 | W | H2H | Match data | Jul 16, 1987* | R32 | Stuttgart Open | ATP 250 | Clay |
| Jan Gunnarsson | 4-6 6-3 5-7 | L | H2H | Match data | Jul 17, 1987* | R16 | Stuttgart Open | ATP 250 | Clay |
| Chip Hooper | 6-3 2-6 6-1 | W | H2H | Match data | Jul 30, 1987* | R32 | Washington Open | ATP 250 | Hard |
| Nduka Odizor | 6-3 6-4 | W | H2H | Match data | Jul 31, 1987* | R16 | Washington Open | ATP 250 | Hard |
| Marty Davis | 6-4 6-4 | W | H2H | Match data | Aug 1, 1987* | QF | Washington Open | ATP 250 | Hard |
| Boris Becker | 3-6 6-3 6-0 | W | H2H | Match data | Aug 1, 1987* | SF | Washington Open | ATP 250 | Hard |
| Ivan Lendl | 1-6 0-6 | L | H2H | Match data | Aug 2, 1987* | F | Washington Open | ATP 250 | Hard |
| Larry Scott | 6-4 6-0 | W | H2H | Match data | Aug 5, 1987* | R64 | Stratton Mountain | ATP 250 | Hard |
| Shelby Cannon | 6-2 6-7 6-2 | W | H2H | Match data | Aug 6, 1987* | R32 | Stratton Mountain | ATP 250 | Hard |
| Amos Mansdorf | 6-4 6-4 | W | H2H | Match data | Aug 7, 1987* | R16 | Stratton Mountain | ATP 250 | Hard |
| John McEnroe | 3-6 2-6 | L | H2H | Match data | Aug 8, 1987* | QF | Stratton Mountain | ATP 250 | Hard |
| Jaime Yzaga | 3-6 6-3 6-4 | W | H2H | Match data | Aug 19, 1987* | R64 | Cincinnati Open | ATP 500 | Hard |
| Christo Van Rensburg | 5-2 (ret.) | W | H2H | Match data | Aug 20, 1987* | R32 | Cincinnati Open | ATP 500 | Hard |
| Wally Masur | 6-7 6-4 6-1 | W | H2H | Match data | Aug 22, 1987* | R16 | Cincinnati Open | ATP 500 | Hard |
| Stefan Edberg | 1-6 3-6 | L | H2H | Match data | Aug 23, 1987* | QF | Cincinnati Open | ATP 500 | Hard |
| Peter Doohan | 6-1 6-2 6-2 | W | H2H | Match data | Sep 3, 1987* | R128 | US Open | Grand Slam | Hard |
| Jay Berger | 4-6 6-2 6-4 6-3 | W | H2H | Match data | Sep 5, 1987* | R64 | US Open | Grand Slam | Hard |
| Guy Forget | 6-4 6-7 7-5 6-4 | W | H2H | Match data | Sep 7, 1987* | R32 | US Open | Grand Slam | Hard |
| Boris Becker | 2-6 6-7 7-6 7-5 6-1 | W | H2H | Match data | Sep 10, 1987* | R16 | US Open | Grand Slam | Hard |
| Jimmy Connors | 6-4 3-6 4-6 0-6 | L | H2H | Match data | Sep 12, 1987* | QF | US Open | Grand Slam | Hard |
| Todd Witsken | 6-2 6-3 | W | H2H | Match data | Sep 24, 1987* | R32 | Los Angeles Open | ATP 250 | Hard |
| Kelly Evernden | 6-3 7-6 | W | H2H | Match data | Sep 25, 1987* | R16 | Los Angeles Open | ATP 250 | Hard |
| Eliot Teltscher | 6-1 6-4 | W | H2H | Match data | Sep 26, 1987* | QF | Los Angeles Open | ATP 250 | Hard |
| David Pate | 3-6 7-6 3-6 | L | H2H | Match data | Sep 26, 1987* | SF | Los Angeles Open | ATP 250 | Hard |
| Tim Wilkison | 5-7 7-6 6-7 | L | H2H | Match data | Oct 1, 1987* | R32 | San Francisco | ATP 250 | Carpet |
| Mike De Palmer | 6-3 6-2 | W | — | Match data | Oct 8, 1987* | R32 | Scottsdale | ATP 250 | Hard |
| Derrick Rostagno | 6-4 6-0 | W | H2H | Match data | Oct 9, 1987* | R16 | Scottsdale | ATP 250 | Hard |
| Johan Kriek | 6-2 6-4 | W | H2H | Match data | Oct 10, 1987* | QF | Scottsdale | ATP 250 | Hard |
| Michael Chang | 6-3 6-4 | W | H2H | Match data | Oct 10, 1987* | SF | Scottsdale | ATP 250 | Hard |
| Eliot Teltscher | 6-2 6-2 | W | H2H | Match data | Oct 11, 1987* | F | Scottsdale | ATP 250 | Hard |
| Raviv Weidenfeld | 6-3 4-6 6-0 | W | H2H | Match data | Oct 15, 1987* | R32 | Tel Aviv | ATP 250 | Hard |
| Shahar Perkiss | 6-1 6-3 | W | H2H | Match data | Oct 16, 1987* | R16 | Tel Aviv | ATP 250 | Hard |
| Gilad Bloom | 6-3 6-3 | W | H2H | Match data | Oct 17, 1987* | QF | Tel Aviv | ATP 250 | Hard |
| Peter Lundgren | 6-3 6-3 | W | H2H | Match data | Oct 17, 1987* | SF | Tel Aviv | ATP 250 | Hard |
| Amos Mansdorf | 6-3 3-6 4-6 | L | H2H | Match data | Oct 18, 1987* | F | Tel Aviv | ATP 250 | Hard |
| Claudio Mezzadri | 6-0 6-3 | W | H2H | Match data | Nov 5, 1987* | R32 | Paris Masters | ATP 250 | Carpet |
| Tomas Smid | 6-2 6-2 | W | H2H | Match data | Nov 6, 1987* | R16 | Paris Masters | ATP 250 | Carpet |
| Kevin Curren | 7-5 6-4 | W | H2H | Match data | Nov 7, 1987* | QF | Paris Masters | ATP 250 | Carpet |
| Michiel Schapers | 7-5 5-7 6-4 | W | H2H | Match data | Nov 7, 1987* | SF | Paris Masters | ATP 250 | Carpet |
| Tim Mayotte | 6-2 3-6 5-7 7-6 3-6 | L | H2H | Match data | Nov 8, 1987* | F | Paris Masters | ATP 250 | Carpet |
| Paul Vojtischek | 6-2 6-7 6-2 | W | H2H | Match data | Nov 13, 1987* | R32 | Frankfurt | ATP 250 | Carpet |
| Christian Bergstrom | 6-2 6-2 | W | H2H | Match data | Nov 14, 1987* | R16 | Frankfurt | ATP 250 | Carpet |
| Jim Pugh | 5-7 6-0 2-6 | L | H2H | Match data | Nov 15, 1987* | QF | Frankfurt | ATP 250 | Carpet |
| Michael Westphal | 6-2 6-0 | W | H2H | Match data | Nov 19, 1987* | R32 | South African Open | ATP 250 | Hard |
| Pieter Aldrich | 6-2 6-1 | W | H2H | Match data | Nov 20, 1987* | R16 | South African Open | ATP 250 | Hard |
| Jakob Hlasek | (w/o) | W | H2H | Match data | Nov 21, 1987* | QF | South African Open | ATP 250 | Hard |
| Andres Gomez | 6-4 6-1 | W | H2H | Match data | Nov 21, 1987* | SF | South African Open | ATP 250 | Hard |
| Pat Cash | 6-7 6-4 6-2 0-6 1-6 | L | H2H | Match data | Nov 22, 1987* | F | South African Open | ATP 250 | Hard |
| Roberto Saad | 5-7 7-6 6-2 | W | H2H | Match data | Nov 26, 1987* | R32 | Itaparica | ATP 250 | Hard |
| Danilo Marcelino | 7-6 6-2 | W | H2H | Match data | Nov 27, 1987* | R16 | Itaparica | ATP 250 | Hard |
| Andre Agassi | 1-6 3-6 | L | H2H | Match data | Nov 28, 1987* | QF | Itaparica | ATP 250 | Hard |
| Jimmy Connors | 6-4 7-6 | W | H2H | Match data | Dec 2, 1987 | RR | ATP Finals | ATP Finals | Carpet |
| Boris Becker | 4-6 6-4 6-4 | W | H2H | Match data | Dec 2, 1987 | RR | ATP Finals | ATP Finals | Carpet |
| Ivan Lendl | 2-6 2-6 | L | H2H | Match data | Dec 2, 1987 | RR | ATP Finals | ATP Finals | Carpet |
| Ivan Lendl | 2-6 4-6 | L | H2H | Match data | Dec 9, 1987* | SF | ATP Finals | ATP Finals | Carpet |
| Pat Cash | 7-6(3) 4-6 7-6(1) 6-4 | W | H2H | Match data | Apr 2, 1988* | QF | Dallas Wct | ATP 250 | Carpet |
| Boris Becker | 4-6 2-6 1-6 | L | H2H | Match data | Apr 2, 1988* | SF | Dallas Wct | ATP 250 | Carpet |
| Leif Shiras | 6-2 6-3 | W | H2H | Match data | Apr 14, 1988* | R32 | Japan Open | ATP 250 | Hard |
| Robert Vant Hof | 6-4 6-2 | W | — | Match data | Apr 15, 1988* | R16 | Japan Open | ATP 250 | Hard |
| David Pate | 6-3 6-2 | W | H2H | Match data | Apr 16, 1988* | QF | Japan Open | ATP 250 | Hard |
| John McEnroe | 3-6 6-0 4-6 | L | H2H | Match data | Apr 16, 1988* | SF | Japan Open | ATP 250 | Hard |
| Michael Robertson | 6-3 6-1 | W | H2H | Match data | Jul 7, 1988* | R32 | U.S. Pro Tennis Championships | ATP 250 | Clay |
| Michael Kures | 5-7 6-4 6-7 | L | H2H | Match data | Jul 8, 1988* | R16 | U.S. Pro Tennis Championships | ATP 250 | Clay |
| Darren Cahill | 6-4 7-6 | W | H2H | Match data | Jul 14, 1988* | R32 | Stuttgart Open | ATP 250 | Clay |
| Ronald Agenor | 6-2 3-6 4-6 | L | H2H | Match data | Jul 15, 1988* | R16 | Stuttgart Open | ATP 250 | Clay |
| Brad Drewett | 3-6 6-3 6-1 | W | H2H | Match data | Jul 21, 1988* | R32 | Washington Open | ATP 250 | Hard |
| Derrick Rostagno | 4-6 3-6 | L | H2H | Match data | Jul 22, 1988* | R16 | Washington Open | ATP 250 | Hard |
| Leonardo Lavalle | 6-7 6-7 | L | H2H | Match data | Jul 27, 1988* | R64 | Stratton Mountain | ATP 250 | Hard |
| Jimmy Brown | 7-6 6-4 | W | — | Match data | Aug 4, 1988* | R32 | U.S. Men's Clay Court Championship | ATP 250 | Hard |
| Jim Pugh | 0-6 4-6 | L | H2H | Match data | Aug 5, 1988* | R16 | U.S. Men's Clay Court Championship | ATP 250 | Hard |
| Pete Sampras | 6-4 6-2 | W | H2H | Match data | Aug 17, 1988* | R64 | Cincinnati Open | ATP 500 | Hard |
| Michiel Schapers | 7-5 6-3 | W | H2H | Match data | Aug 18, 1988* | R32 | Cincinnati Open | ATP 500 | Hard |
| Aaron Krickstein | 0-6 3-6 | L | H2H | Match data | Aug 20, 1988* | R16 | Cincinnati Open | ATP 500 | Hard |
| Milan Srejber | 6-3 6-3 6-2 | W | H2H | Match data | Aug 31, 1988* | R128 | US Open | Grand Slam | Hard |
| Jaime Yzaga | 6-1 0-6 4-6 2-6 | L | H2H | Match data | Sep 2, 1988* | R64 | US Open | Grand Slam | Hard |
| Michael Tauson | 6-2 7-5 6-1 | W | H2H | Match data | Sep 23, 1988* | R64 | Seoul Olympics | Olympics | Hard |
| Andrei Cherkasov | 6-4 1-6 6-1 6-2 | W | H2H | Match data | Sep 25, 1988* | R32 | Seoul Olympics | Olympics | Hard |
| Robert Seguso | 6-2 6-1 6-2 | W | H2H | Match data | Sep 27, 1988* | R16 | Seoul Olympics | Olympics | Hard |
| Martin Jaite | 5-7 6-1 7-6(1) 6-3 | W | H2H | Match data | Sep 29, 1988* | QF | Seoul Olympics | Olympics | Hard |
Estimated from the tournament schedule where an exact match date is unavailable. Arrows show an edition's recorded category and documented modern equivalent; unresolved editions keep their recorded category. Mapping details.