Match log updated: 2026-08-31 13:51 UTC
Darren Cahill — ATP Match Log
Main draw matches: 248 | W: 132 | L: 116 | Win %: 53.2%
| Opponent | Score | Result | H2H | Match Data | Date ↑ | Round | Tournament | Category | Surface |
|---|---|---|---|---|---|---|---|---|---|
| Brad Drewett | 3-6 2-6 | L | H2H | Match data | Oct 18, 1984* | R32 | Melbourne Indoor | ATP 250 | Carpet |
| Rodney Harmon | 6-7 1-6 6-4 7-6 6-2 | W | H2H | Match data | Nov 28, 1984* | R128 | Australian Open | Grand Slam | Grass |
| Dan Cassidy | 6-7 3-6 6-7 | L | H2H | Match data | Nov 30, 1984* | R64 | Australian Open | Grand Slam | Grass |
| Miloslav Mecir | 5-7 5-7 | L | H2H | Match data | Dec 20, 1984* | R32 | Adelaide International | ATP 250 | Grass |
| Brian Levine | 6-7 6-2 6-3 | W | H2H | Match data | Dec 27, 1984* | R32 | Melbourne | ATP 250 | Grass |
| Jakob Hlasek | 1-6 7-6 6-7 | L | H2H | Match data | Dec 28, 1984* | R16 | Melbourne | ATP 250 | Grass |
| Mark Dickson | 3-6 6-2 6-1 2-6 14-12 | W | H2H | Match data | May 29, 1985* | R128 | Roland Garros | Grand Slam | Clay |
| Dan Cassidy | 6-0 6-1 6-2 | W | H2H | Match data | May 31, 1985* | R64 | Roland Garros | Grand Slam | Clay |
| Tomas Smid | 2-6 1-6 1-6 | L | H2H | Match data | Jun 2, 1985* | R32 | Roland Garros | Grand Slam | Clay |
| Cassio Motta | 2-6 4-6 | L | H2H | Match data | Jul 11, 1985* | R32 | Swiss Open Gstaad | ATP 250 | Clay |
| Peter Carlsson | 2-6 6-1 7-5 | W | H2H | Match data | Jul 18, 1985* | R32 | Swedish Open | ATP 250 | Clay |
| Henrik Sundstrom | 2-6 2-6 | L | H2H | Match data | Jul 19, 1985* | R16 | Swedish Open | ATP 250 | Clay |
| Trevor Allan | 6-1 4-6 6-3 | W | H2H | Match data | Jul 25, 1985* | R32 | Dutch Open | ATP 250 | Clay |
| Goran Prpic | 6-3 3-6 6-3 | W | H2H | Match data | Jul 26, 1985* | R16 | Dutch Open | ATP 250 | Clay |
| Kent Carlsson | 2-6 2-6 | L | H2H | Match data | Jul 27, 1985* | QF | Dutch Open | ATP 250 | Clay |
| Francesco Cancellotti | 6-2 6-4 | W | H2H | Match data | Aug 7, 1985* | R64 | Austrian Open Kitzbühel | ATP 250 | Clay |
| Mark Buckley | 7-6 6-2 | W | H2H | Match data | Aug 8, 1985* | R32 | Austrian Open Kitzbühel | ATP 250 | Clay |
| Sergio Casal | 3-6 6-7 | L | H2H | Match data | Aug 9, 1985* | R16 | Austrian Open Kitzbühel | ATP 250 | Clay |
| Tom Cain | 6-4 2-6 6-3 | W | H2H | Match data | Oct 10, 1985* | R32 | Brisbane International | ATP 250 | Carpet |
| Bud Schultz | 6-2 1-6 3-6 | L | H2H | Match data | Oct 11, 1985* | R16 | Brisbane International | ATP 250 | Carpet |
| Glenn Layendecker | 1-6 7-5 6-2 | W | H2H | Match data | Oct 17, 1985* | R32 | Sydney Indoor | ATP 250 | Hard |
| Andres Gomez | 0-6 2-6 | L | H2H | Match data | Oct 18, 1985* | R16 | Sydney Indoor | ATP 250 | Hard |
| Mark Woodforde | 5-7 4-6 | L | H2H | Match data | Oct 24, 1985* | R32 | Melbourne Indoor | ATP 250 | Carpet |
| Tarik Benhabiles | 6-4 6-4 4-6 6-2 | W | H2H | Match data | Nov 27, 1985* | R128 | Australian Open | Grand Slam | Grass |
| David Pate | 3-6 7-6 6-3 6-0 | W | H2H | Match data | Nov 29, 1985* | R64 | Australian Open | Grand Slam | Grass |
| Tim Gullikson | 4-6 3-6 6-3 4-6 | L | — | Match data | Dec 1, 1985* | R32 | Australian Open | Grand Slam | Grass |
| Danie Visser | 3-6 6-7 | L | H2H | Match data | Dec 11, 1985* | R64 | Sydney International | ATP 250 | Grass |
| John Frawley | 4-6 6-7 | L | — | Match data | Dec 19, 1985* | R32 | Adelaide International | ATP 250 | Grass |
| Peter Doohan | 4-6 4-6 | L | H2H | Match data | Dec 26, 1985* | R32 | Melbourne | ATP 250 | Grass |
| Thomas Muster | 6-2 6-3 | W | H2H | Match data | Apr 10, 1986* | R32 | Bari | ATP 250 | Clay |
| Lawson Duncan | 3-6 3-6 | L | H2H | Match data | Apr 11, 1986* | R16 | Bari | ATP 250 | Clay |
| Julio Goes | 4-6 6-3 6-2 6-0 | W | H2H | Match data | May 28, 1986* | R128 | Roland Garros | Grand Slam | Clay |
| Ulf Stenlund | 3-6 1-6 0-6 | L | H2H | Match data | May 30, 1986* | R64 | Roland Garros | Grand Slam | Clay |
| Derrick Rostagno | 7-6 5-7 6-4 | W | H2H | Match data | Jun 18, 1986* | R64 | Bristol | ATP 250 | Grass |
| Todd Witsken | 7-6 6-4 | W | H2H | Match data | Jun 19, 1986* | R32 | Bristol | ATP 250 | Grass |
| Tim Wilkison | 1-6 7-6 5-7 | L | H2H | Match data | Jun 20, 1986* | R16 | Bristol | ATP 250 | Grass |
| Tomas Smid | 4-6 3-6 5-7 | L | H2H | Match data | Jun 25, 1986* | R128 | Wimbledon | Grand Slam | Grass |
| Sergio Casal | 1-6 6-3 6-7 2-6 | L | H2H | Match data | Aug 28, 1986* | R128 | US Open | Grand Slam | Hard |
| Tomm Warneke | 6-2 6-4 | W | H2H | Match data | Oct 16, 1986* | R32 | Sydney Indoor | ATP 250 | Hard |
| Glenn Layendecker | 5-7 4-6 | L | H2H | Match data | Oct 17, 1986* | R16 | Sydney Indoor | ATP 250 | Hard |
| Johan Carlsson | 7-6 6-7 3-6 | L | H2H | Match data | Jan 2, 1987* | R32 | Adelaide International | ATP 250 | Grass |
| Mark Woodforde | 1-6 6-3 2-6 | L | H2H | Match data | Jan 8, 1987* | R32 | ASB Classic | ATP 250 | Hard |
| Shane Barr | 3-6 4-6 4-6 | L | H2H | Match data | Jan 14, 1987* | R128 | Australian Open | Grand Slam | Grass |
| Bill Scanlon | 4-6 3-6 | L | H2H | Match data | Jan 29, 1987* | R32 | Sydney International | ATP 250 | Grass |
| Corrado Aprili | 6-3 6-1 6-3 | W | H2H | Match data | Feb 24, 1987* | R128 | Miami Open | ATP 500 | Hard |
| Gilad Bloom | 4-6 6-3 7-5 6-2 | W | H2H | Match data | Feb 25, 1987* | R64 | Miami Open | ATP 500 | Hard |
| Jimmy Connors | 3-6 3-6 1-6 | L | H2H | Match data | Feb 26, 1987* | R32 | Miami Open | ATP 500 | Hard |
| Miloslav Mecir | 2-6 3-6 | L | H2H | Match data | Mar 19, 1987* | R32 | ABN AMRO Open | ATP 250 | Carpet |
| Wally Masur | 6-3 2-6 2-6 | L | H2H | Match data | Mar 26, 1987* | R32 | Nancy | ATP 250 | Carpet |
| Ronald Agenor | 0-6 6-4 7-5 | W | H2H | Match data | Apr 29, 1987* | R64 | Hamburg Open | ATP 250 | Clay |
| Ivan Lendl | 2-6 1-6 | L | H2H | Match data | Apr 30, 1987* | R32 | Hamburg Open | ATP 250 | Clay |
| Mark Kratzmann | 6-0 6-3 4-6 6-4 | W | H2H | Match data | May 27, 1987* | R128 | Roland Garros | Grand Slam | Clay |
| Michael Robertson | 6-4 7-6 6-3 | W | H2H | Match data | May 29, 1987* | R64 | Roland Garros | Grand Slam | Clay |
| Joakim Nystrom | 4-6 6-7 4-6 | L | H2H | Match data | May 31, 1987* | R32 | Roland Garros | Grand Slam | Clay |
| Mel Purcell | 4-6 6-7 | L | H2H | Match data | Jun 10, 1987* | R64 | Queen's Club Championships | ATP 250 | Grass |
| Corrado Aprili | 6-3 3-6 6-1 | W | H2H | Match data | Jul 16, 1987* | R32 | Bordeaux | ATP 250 | Clay |
| Ronald Agenor | 6-7 6-4 3-6 | L | H2H | Match data | Jul 17, 1987* | R16 | Bordeaux | ATP 250 | Clay |
| Karel Novacek | 6-3 6-3 | W | H2H | Match data | Aug 5, 1987* | R64 | Austrian Open Kitzbühel | ATP 250 | Clay |
| Simone Colombo | 6-3 6-3 | W | — | Match data | Aug 6, 1987* | R32 | Austrian Open Kitzbühel | ATP 250 | Clay |
| Tomas Smid | 6-7 7-6 7-6 | W | H2H | Match data | Aug 7, 1987* | R16 | Austrian Open Kitzbühel | ATP 250 | Clay |
| Ricki Osterthun | 6-3 1-6 7-5 | W | H2H | Match data | Aug 8, 1987* | QF | Austrian Open Kitzbühel | ATP 250 | Clay |
| Miloslav Mecir | 1-6 2-6 | L | H2H | Match data | Aug 8, 1987* | SF | Austrian Open Kitzbühel | ATP 250 | Clay |
| Dan Goldie | 2-6 2-6 | L | H2H | Match data | Aug 27, 1987* | R32 | Rye Brook | ATP 250 | Hard |
| Michael Kures | 6-2 7-5 6-4 | W | H2H | Match data | Sep 3, 1987* | R128 | US Open | Grand Slam | Hard |
| Ken Flach | 6-1 4-6 6-3 1-6 6-7 | L | H2H | Match data | Sep 5, 1987* | R64 | US Open | Grand Slam | Hard |
| Robert Seguso | 6-2 6-7 7-6 | W | H2H | Match data | Oct 8, 1987* | R32 | Brisbane International | ATP 250 | Hard |
| Eric Jelen | 4-6 3-6 | L | H2H | Match data | Oct 9, 1987* | R16 | Brisbane International | ATP 250 | Hard |
| Broderick Dyke | 6-4 3-6 6-3 | W | H2H | Match data | Oct 15, 1987* | R32 | Sydney Indoor | ATP 250 | Hard |
| Scott Davis | 3-6 6-3 2-6 | L | H2H | Match data | Oct 16, 1987* | R16 | Sydney Indoor | ATP 250 | Hard |
| John Ross | 6-1 6-3 | W | — | Match data | Oct 23, 1987* | R32 | Tokyo Indoor | ATP 250 | Carpet |
| Paul Annacone | 4-6 2-6 | L | H2H | Match data | Oct 24, 1987* | R16 | Tokyo Indoor | ATP 250 | Carpet |
| Tony Mmoh | 7-6 6-2 | W | H2H | Match data | Oct 29, 1987* | R32 | Hong Kong Open | ATP 250 | Hard |
| Gary Muller | 6-4 7-6 | W | — | Match data | Oct 30, 1987* | R16 | Hong Kong Open | ATP 250 | Hard |
| John Ross | 6-4 4-6 6-4 | W | — | Match data | Oct 31, 1987* | QF | Hong Kong Open | ATP 250 | Hard |
| Eliot Teltscher | 5-7 0-6 | L | H2H | Match data | Oct 31, 1987* | SF | Hong Kong Open | ATP 250 | Hard |
| Patrick Baur | 7-6 5-7 2-6 | L | H2H | Match data | Dec 31, 1987* | R32 | Adelaide International | ATP 250 | Hard |
| Paul Chamberlin | 6-3 4-6 6-3 | W | H2H | Match data | Jan 7, 1988* | R32 | Sydney International | ATP 250 | Grass |
| Andrew Castle | 7-6 6-3 | W | H2H | Match data | Jan 8, 1988* | R16 | Sydney International | ATP 250 | Grass |
| Andrei Chesnokov | 3-6 5-7 | L | H2H | Match data | Jan 9, 1988* | QF | Sydney International | ATP 250 | Grass |
| Shane Barr | 6-1 6-3 4-6 6-1 | W | H2H | Match data | Jan 13, 1988* | R128 | Australian Open | Grand Slam | Hard |
| Todd Witsken | 4-6 5-7 2-6 | L | H2H | Match data | Jan 15, 1988* | R64 | Australian Open | Grand Slam | Hard |
| Libor Pimek | 4-6 3-6 | L | H2H | Match data | Feb 11, 1988* | R32 | ABN AMRO Open | ATP 250 | Carpet |
| Marian Vajda | 2-6 6-0 6-4 | W | H2H | Match data | Mar 2, 1988* | R64 | Indian Wells Open | ATP 500 | Hard |
| Aaron Krickstein | 6-4 6-4 | W | H2H | Match data | Mar 3, 1988* | R32 | Indian Wells Open | ATP 500 | Hard |
| Miloslav Mecir | 6-2 0-6 4-6 | L | H2H | Match data | Mar 5, 1988* | R16 | Indian Wells Open | ATP 500 | Hard |
| Tim Wilkison | 7-5 6-4 6-7 6-3 | W | H2H | Match data | Mar 15, 1988* | R128 | Miami Open | ATP 500 | Hard |
| Andrei Chesnokov | 2-6 4-6 6-3 4-6 | L | H2H | Match data | Mar 16, 1988* | R64 | Miami Open | ATP 500 | Hard |
| Andreas Lesch | 3-6 5-7 | L | H2H | Match data | Apr 14, 1988* | R32 | Nice | ATP 250 | Clay |
| Alberto Mancini | 6-4 3-6 2-6 | L | H2H | Match data | Apr 20, 1988* | R64 | Monte-Carlo Masters | ATP 250 | Clay |
| Nicklas Kroon | 6-2 6-0 | W | H2H | Match data | Apr 27, 1988* | R64 | Hamburg Open | ATP 250 | Clay |
| Martin Jaite | 2-6 7-6 6-1 | W | H2H | Match data | Apr 28, 1988* | R32 | Hamburg Open | ATP 250 | Clay |
| Guillermo Vilas | 3-6 6-4 1-6 | L | H2H | Match data | Apr 29, 1988* | R16 | Hamburg Open | ATP 250 | Clay |
| Hans Schwaier | 6-1 4-6 6-7 | L | H2H | Match data | May 5, 1988* | R32 | Munich Open | ATP 250 | Clay |
| Eduardo Bengoechea | 7-6 6-7 7-5 2-6 3-6 | L | H2H | Match data | May 25, 1988* | R128 | Roland Garros | Grand Slam | Clay |
| Ricardo Acuna | 6-7 6-3 9-7 | W | H2H | Match data | Jun 8, 1988* | R64 | Queen's Club Championships | ATP 250 | Grass |
| Ken Flach | 2-6 7-5 6-3 | W | H2H | Match data | Jun 9, 1988* | R32 | Queen's Club Championships | ATP 250 | Grass |
| Pat Cash | 7-6 6-4 | W | H2H | Match data | Jun 10, 1988* | R16 | Queen's Club Championships | ATP 250 | Grass |
| Kevin Curren | 7-5 7-6 | W | H2H | Match data | Jun 11, 1988* | QF | Queen's Club Championships | ATP 250 | Grass |
| Boris Becker | 2-6 4-6 | L | H2H | Match data | Jun 11, 1988* | SF | Queen's Club Championships | ATP 250 | Grass |
| Gary Muller | 6-7 6-2 6-2 6-0 | W | — | Match data | Jun 22, 1988* | R128 | Wimbledon | Grand Slam | Grass |
| Ivan Lendl | 7-5 2-6 4-6 4-6 | L | H2H | Match data | Jun 24, 1988* | R64 | Wimbledon | Grand Slam | Grass |
| Marko Ostoja | 6-4 6-2 | W | H2H | Match data | Jul 7, 1988* | R32 | Swiss Open Gstaad | ATP 250 | Clay |
| Tomas Smid | 6-1 6-4 | W | H2H | Match data | Jul 8, 1988* | R16 | Swiss Open Gstaad | ATP 250 | Clay |
| Emilio Sanchez | 4-6 7-6 7-6 | W | H2H | Match data | Jul 9, 1988* | QF | Swiss Open Gstaad | ATP 250 | Clay |
| Horst Skoff | 6-1 6-1 | W | H2H | Match data | Jul 9, 1988* | SF | Swiss Open Gstaad | ATP 250 | Clay |
| Jakob Hlasek | 6-3 6-4 7-6 | W | H2H | Match data | Jul 10, 1988* | F | Swiss Open Gstaad | ATP 250 | Clay |
| Guillermo Vilas | 6-3 1-6 6-3 | W | H2H | Match data | Jul 13, 1988* | R64 | Stuttgart Open | ATP 250 | Clay |
| Brad Gilbert | 4-6 6-7 | L | H2H | Match data | Jul 14, 1988* | R32 | Stuttgart Open | ATP 250 | Clay |
| Brian Page | 6-3 6-3 | W | H2H | Match data | Jul 21, 1988* | R32 | Washington Open | ATP 250 | Hard |
| Chris Pridham | 6-2 6-1 | W | H2H | Match data | Jul 22, 1988* | R16 | Washington Open | ATP 250 | Hard |
| Derrick Rostagno | 4-6 6-7 | L | H2H | Match data | Jul 23, 1988* | QF | Washington Open | ATP 250 | Hard |
| Kelly Evernden | 6-3 6-0 | W | H2H | Match data | Jul 27, 1988* | R64 | Stratton Mountain | ATP 250 | Hard |
| Dan Cassidy | 6-1 6-2 | W | H2H | Match data | Jul 28, 1988* | R32 | Stratton Mountain | ATP 250 | Hard |
| Michael Robertson | 6-2 6-7 6-2 | W | H2H | Match data | Jul 29, 1988* | R16 | Stratton Mountain | ATP 250 | Hard |
| Roger Smith | 6-3 4-6 6-2 | W | H2H | Match data | Jul 30, 1988* | QF | Stratton Mountain | ATP 250 | Hard |
| Paul Annacone | 4-6 3-6 | L | H2H | Match data | Jul 30, 1988* | SF | Stratton Mountain | ATP 250 | Hard |
| Wally Masur | 6-3 3-6 1-6 | L | H2H | Match data | Aug 17, 1988* | R64 | Cincinnati Open | ATP 500 | Hard |
| Lawson Duncan | 6-0 6-0 6-2 | W | H2H | Match data | Aug 31, 1988* | R128 | US Open | Grand Slam | Hard |
| Boris Becker | 6-3 6-3 6-2 | W | H2H | Match data | Sep 2, 1988* | R64 | US Open | Grand Slam | Hard |
| Marcelo Ingaramo | (w/o) | W | H2H | Match data | Sep 4, 1988* | R32 | US Open | Grand Slam | Hard |
| Martin Laurendeau | 6-4 6-4 6-3 | W | H2H | Match data | Sep 7, 1988* | R16 | US Open | Grand Slam | Hard |
| Aaron Krickstein | 6-2 5-7 7-6 5-7 6-3 | W | H2H | Match data | Sep 9, 1988* | QF | US Open | Grand Slam | Hard |
| Mats Wilander | 4-6 4-6 2-6 | L | H2H | Match data | Sep 11, 1988* | SF | US Open | Grand Slam | Hard |
| Alex Antonitsch | 6-2 6-4 6-7(2) 6-2 | W | H2H | Match data | Sep 23, 1988* | R64 | Seoul Olympics | Olympics | Hard |
| Robert Seguso | 3-6 6-7(3) 7-6(8) 2-6 | L | H2H | Match data | Sep 25, 1988* | R32 | Seoul Olympics | Olympics | Hard |
| Shane Barr | 2-6 1-6 | L | H2H | Match data | Oct 7, 1988* | R32 | Brisbane International | ATP 250 | Hard |
| Todd Woodbridge | 6-4 6-4 | W | H2H | Match data | Oct 13, 1988* | R32 | Sydney Indoor | ATP 250 | Hard |
| Grant Connell | 6-3 6-7 2-6 | L | H2H | Match data | Oct 14, 1988* | R16 | Sydney Indoor | ATP 250 | Hard |
| Shuzo Matsuoka | 6-7 1-6 | L | H2H | Match data | Oct 21, 1988* | R32 | Tokyo Indoor | ATP 250 | Carpet |
| Aaron Krickstein | 6-7 6-7 | L | H2H | Match data | Oct 27, 1988* | R32 | Paris Masters | ATP 250 | Carpet |
| Mark Kratzmann | 6-7 1-6 | L | H2H | Match data | Jan 5, 1989* | R32 | Adelaide International | ATP 250 | Hard |
| Carl Uwe Steeb | 3-6 6-4 1-6 | L | H2H | Match data | Jan 12, 1989* | R32 | Sydney International | ATP 250 | Hard |
| Jakob Hlasek | 6-4 6-7 6-3 7-6 | W | H2H | Match data | Jan 18, 1989* | R128 | Australian Open | Grand Slam | Hard |
| Olivier Delaitre | 4-6 6-1 6-1 6-1 | W | H2H | Match data | Jan 20, 1989* | R64 | Australian Open | Grand Slam | Hard |
| Magnus Gustafsson | 7-6 6-0 5-7 2-6 4-6 | L | H2H | Match data | Jan 22, 1989* | R32 | Australian Open | Grand Slam | Hard |
| Jorge Lozano | 6-2 6-7 6-3 | W | H2H | Match data | Feb 9, 1989* | R32 | ABN AMRO Open | ATP 250 | Carpet |
| Christian Saceanu | 7-6 7-6 | W | H2H | Match data | Feb 10, 1989* | R16 | ABN AMRO Open | ATP 250 | Carpet |
| Marty Davis | 6-3 7-6 | W | H2H | Match data | Feb 11, 1989* | QF | ABN AMRO Open | ATP 250 | Carpet |
| Anders Jarryd | 2-6 4-6 | L | H2H | Match data | Feb 11, 1989* | SF | ABN AMRO Open | ATP 250 | Carpet |
| Eric Winogradsky | 4-6 6-3 7-6 | W | H2H | Match data | Mar 2, 1989* | R32 | Nancy | ATP 250 | Hard |
| Johan Carlsson | 4-6 1-6 | L | H2H | Match data | Mar 3, 1989* | R16 | Nancy | ATP 250 | Hard |
| Jaime Yzaga | 3-6 6-3 6-1 | W | H2H | Match data | Mar 15, 1989* | R64 | Indian Wells Open | ATP 500 | Hard |
| Brad Gilbert | 4-6 4-6 | L | H2H | Match data | Mar 16, 1989* | R32 | Indian Wells Open | ATP 500 | Hard |
| Yahiya Doumbia | 3-6 7-6 6-4 6-2 | W | H2H | Match data | Mar 21, 1989* | R128 | Miami Open | ATP 500 | Hard |
| Brad Drewett | 6-7 6-1 6-3 3-6 6-4 | W | H2H | Match data | Mar 22, 1989* | R64 | Miami Open | ATP 500 | Hard |
| Jim Grabb | 4-6 6-0 6-7 1-6 | L | H2H | Match data | Mar 23, 1989* | R32 | Miami Open | ATP 500 | Hard |
| Tomas Carbonell | 3-6 3-6 | L | H2H | Match data | May 10, 1989* | R64 | Hamburg Open | ATP 250 | Clay |
| Franco Davin | 1-6 7-5 6-2 | W | H2H | Match data | May 17, 1989* | R64 | Italian Open | ATP 500 | Clay |
| Martin Strelba | 6-3 2-6 6-2 | W | H2H | Match data | May 18, 1989* | R32 | Italian Open | ATP 500 | Clay |
| Jordi Arrese | 6-3 3-6 5-7 | L | H2H | Match data | May 20, 1989* | R16 | Italian Open | ATP 500 | Clay |
| Neil Broad | 6-4 6-1 6-4 | W | H2H | Match data | May 31, 1989* | R128 | Roland Garros | Grand Slam | Clay |
| Jan Gunnarsson | 5-7 6-3 6-2 7-5 | W | H2H | Match data | Jun 2, 1989* | R64 | Roland Garros | Grand Slam | Clay |
| Ivan Lendl | 6-7 3-6 3-6 | L | H2H | Match data | Jun 4, 1989* | R32 | Roland Garros | Grand Slam | Clay |
| Grant Connell | 5-7 6-2 6-4 | W | H2H | Match data | Jun 14, 1989* | R64 | Queen's Club Championships | ATP 250 | Grass |
| Michael Stich | 6-7 3-6 | L | H2H | Match data | Jun 15, 1989* | R32 | Queen's Club Championships | ATP 250 | Grass |
| John McEnroe | 6-4 6-4 2-6 3-6 6-8 | L | H2H | Match data | Jun 28, 1989* | R128 | Wimbledon | Grand Slam | Grass |
| Alex Antonitsch | 4-6 1-6 | L | H2H | Match data | Jul 27, 1989* | R32 | Stuttgart Open | ATP 250 | Clay |
| Jimmy Brown | 7-5 6-1 6-2 | W | — | Match data | Aug 30, 1989* | R128 | US Open | Grand Slam | Hard |
| Emilio Sanchez | 3-6 7-6 4-6 4-6 | L | H2H | Match data | Sep 1, 1989* | R64 | US Open | Grand Slam | Hard |
| Christo Van Rensburg | 1-6 7-5 6-1 | W | H2H | Match data | Sep 21, 1989* | R32 | Los Angeles Open | ATP 250 | Hard |
| Jimmy Arias | 6-3 6-2 | W | H2H | Match data | Sep 22, 1989* | R16 | Los Angeles Open | ATP 250 | Hard |
| Michael Chang | 1-6 3-6 | L | H2H | Match data | Sep 23, 1989* | QF | Los Angeles Open | ATP 250 | Hard |
| Anders Jarryd | 1-6 0-6 | L | H2H | Match data | Sep 28, 1989* | R32 | San Francisco | ATP 250 | Carpet |
| Peter Doohan | 6-3 6-3 | W | H2H | Match data | Oct 5, 1989* | R32 | Brisbane International | ATP 250 | Hard |
| Johan Anderson | 6-3 7-5 | W | H2H | Match data | Oct 6, 1989* | R16 | Brisbane International | ATP 250 | Hard |
| Todd Woodbridge | 4-6 7-5 4-6 | L | H2H | Match data | Oct 7, 1989* | QF | Brisbane International | ATP 250 | Hard |
| Vijay Amritraj | 6-4 6-0 | W | H2H | Match data | Oct 12, 1989* | R32 | Sydney Indoor | ATP 250 | Hard |
| Nicklas Kroon | 0-6 4-6 | L | H2H | Match data | Oct 13, 1989* | R16 | Sydney Indoor | ATP 250 | Hard |
| Richard Matuszewski | 7-6 3-6 6-2 | W | H2H | Match data | Oct 20, 1989* | R32 | Tokyo Indoor | ATP 250 | Carpet |
| Dan Goldie | 7-6 6-4 | W | H2H | Match data | Oct 21, 1989* | R16 | Tokyo Indoor | ATP 250 | Carpet |
| Ronald Agenor | 3-6 7-6 6-4 | W | H2H | Match data | Oct 22, 1989* | QF | Tokyo Indoor | ATP 250 | Carpet |
| Carl Uwe Steeb | 4-6 4-6 | L | H2H | Match data | Oct 22, 1989* | SF | Tokyo Indoor | ATP 250 | Carpet |
| Andres Gomez | 6-4 3-6 6-1 2-6 3-6 | L | H2H | Match data | Jan 17, 1990* | R128 | Australian Open | Grand Slam | Hard |
| Jim Courier | 0-6 3-6 | L | H2H | Match data | Feb 14, 1990* | R64 | Toronto Indoor | ATP Championship Series → modern equivalent ATP 500 | Carpet |
| Michiel Schapers | 7-6 3-6 6-7 | L | H2H | Match data | Feb 21, 1990* | R64 | Philadelphia | ATP Championship Series → modern equivalent ATP 500 | Carpet |
| Tim Wilkison | 6-7 7-6 7-5 | W | H2H | Match data | Mar 1, 1990* | R32 | Memphis | ATP World Series → modern equivalent ATP 250 | Hard |
| Glenn Layendecker | 4-6 4-6 | L | H2H | Match data | Mar 2, 1990* | R16 | Memphis | ATP World Series → modern equivalent ATP 250 | Hard |
| Andres Gomez | 7-5 6-4 | W | H2H | Match data | Mar 7, 1990* | R64 | Indian Wells Open | Masters 1000 | Hard |
| Christo Van Rensburg | 6-1 6-3 | W | H2H | Match data | Mar 8, 1990* | R32 | Indian Wells Open | Masters 1000 | Hard |
| Jim Courier | 4-6 2-6 | L | H2H | Match data | Mar 10, 1990* | R16 | Indian Wells Open | Masters 1000 | Hard |
| Mark Kratzmann | 3-6 6-4 3-6 | L | H2H | Match data | Mar 17, 1990* | R128 | Miami Open | Masters 1000 | Hard |
| Anders Jarryd | 2-6 6-4 1-6 7-6 3-6 | L | H2H | Match data | May 30, 1990* | R128 | Roland Garros | Grand Slam | Clay |
| Guillaume Raoux | 6-4 7-6 | W | H2H | Match data | Jun 13, 1990* | R64 | Queen's Club Championships | ATP World Series → modern equivalent ATP 250 | Grass |
| Christo Van Rensburg | 3-6 6-7 | L | H2H | Match data | Jun 14, 1990* | R32 | Queen's Club Championships | ATP World Series → modern equivalent ATP 250 | Grass |
| Martin Wostenholme | 6-2 6-2 6-0 | W | H2H | Match data | Jun 27, 1990* | R128 | Wimbledon | Grand Slam | Grass |
| Paul Haarhuis | 5-7 7-5 6-7 6-4 3-6 | L | H2H | Match data | Jun 29, 1990* | R64 | Wimbledon | Grand Slam | Grass |
| Broderick Dyke | 6-3 6-3 | W | H2H | Match data | Jul 12, 1990* | R32 | Newport | ATP World Series → modern equivalent ATP 250 | Grass |
| Todd Martin | (w/o) | W | H2H | Match data | Jul 13, 1990* | R16 | Newport | ATP World Series → modern equivalent ATP 250 | Grass |
| Mark Kratzmann | 6-2 6-4 | W | H2H | Match data | Jul 14, 1990* | QF | Newport | ATP World Series → modern equivalent ATP 250 | Grass |
| Eric Jelen | 7-6 6-3 | W | H2H | Match data | Jul 14, 1990* | SF | Newport | ATP World Series → modern equivalent ATP 250 | Grass |
| Pieter Aldrich | 6-7 6-1 1-6 | L | H2H | Match data | Jul 15, 1990* | F | Newport | ATP World Series → modern equivalent ATP 250 | Grass |
| Christo Van Rensburg | 6-4 6-0 | W | H2H | Match data | Jul 18, 1990* | R64 | Washington Open | ATP Championship Series → modern equivalent ATP 500 | Hard |
| Miguel Nido | 4-6 6-0 6-2 | W | H2H | Match data | Jul 19, 1990* | R32 | Washington Open | ATP Championship Series → modern equivalent ATP 500 | Hard |
| Richey Reneberg | 4-6 6-2 5-7 | L | H2H | Match data | Jul 20, 1990* | R16 | Washington Open | ATP Championship Series → modern equivalent ATP 500 | Hard |
| Alexander Volkov | 5-7 7-5 6-3 | W | H2H | Match data | Jul 25, 1990* | R64 | Canadian Open | Masters 1000 | Hard |
| Brad Pearce | 6-4 6-4 | W | H2H | Match data | Jul 26, 1990* | R32 | Canadian Open | Masters 1000 | Hard |
| Andre Agassi | 2-6 4-6 | L | H2H | Match data | Jul 28, 1990* | R16 | Canadian Open | Masters 1000 | Hard |
| Tim Mayotte | 1-6 6-4 7-5 | W | H2H | Match data | Aug 8, 1990* | R64 | Cincinnati Open | Masters 1000 | Hard |
| Mats Wilander | 6-3 6-2 | W | H2H | Match data | Aug 9, 1990* | R32 | Cincinnati Open | Masters 1000 | Hard |
| Andres Gomez | 6-7 3-6 | L | H2H | Match data | Aug 11, 1990* | R16 | Cincinnati Open | Masters 1000 | 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.