Match log updated: 2026-05-28 18:14 UTC
Darren Cahill — ATP Match Log
Main draw matches: 246 | W: 131 | L: 115 | Win %: 53.3%
| Date ↑ | Tournament | Category | Round | Surface | Opponent | Score | Result | H2H | Match |
|---|---|---|---|---|---|---|---|---|---|
| Oct 18, 1984* | Melbourne Indoor | ATP 250 | R32 | Carpet | Brad Drewett | 3-6 2-6 | L | H2H | Match data |
| Nov 28, 1984* | Australian Open | Grand Slam | R128 | Grass | Rodney Harmon | 6-7 1-6 6-4 7-6 6-2 | W | H2H | Match data |
| Nov 30, 1984* | Australian Open | Grand Slam | R64 | Grass | Dan Cassidy | 6-7 3-6 6-7 | L | H2H | Match data |
| Dec 20, 1984* | Adelaide | ATP 250 | R32 | Grass | Miloslav Mecir | 5-7 5-7 | L | H2H | Match data |
| Dec 27, 1984* | Melbourne | ATP 250 | R32 | Grass | Brian Levine | 6-7 6-2 6-3 | W | H2H | Match data |
| Dec 28, 1984* | Melbourne | ATP 250 | R16 | Grass | Jakob Hlasek | 1-6 7-6 6-7 | L | H2H | Match data |
| May 29, 1985* | Roland Garros | Grand Slam | R128 | Clay | Mark Dickson | 3-6 6-2 6-1 2-6 14-12 | W | H2H | Match data |
| May 31, 1985* | Roland Garros | Grand Slam | R64 | Clay | Dan Cassidy | 6-0 6-1 6-2 | W | H2H | Match data |
| Jun 2, 1985* | Roland Garros | Grand Slam | R32 | Clay | Tomas Smid | 2-6 1-6 1-6 | L | H2H | Match data |
| Jul 11, 1985* | Gstaad | ATP 250 | R32 | Clay | Cassio Motta | 2-6 4-6 | L | H2H | Match data |
| Jul 18, 1985* | Bastad | ATP 250 | R32 | Clay | Peter Carlsson | 2-6 6-1 7-5 | W | H2H | Match data |
| Jul 19, 1985* | Bastad | ATP 250 | R16 | Clay | Henrik Sundstrom | 2-6 2-6 | L | H2H | Match data |
| Jul 25, 1985* | Hilversum | ATP 250 | R32 | Clay | Trevor Allan | 6-1 4-6 6-3 | W | H2H | Match data |
| Jul 26, 1985* | Hilversum | ATP 250 | R16 | Clay | Goran Prpic | 6-3 3-6 6-3 | W | H2H | Match data |
| Jul 27, 1985* | Hilversum | ATP 250 | QF | Clay | Kent Carlsson | 2-6 2-6 | L | H2H | Match data |
| Aug 7, 1985* | Kitzbuhel | ATP 250 | R64 | Clay | Francesco Cancellotti | 6-2 6-4 | W | H2H | Match data |
| Aug 8, 1985* | Kitzbuhel | ATP 250 | R32 | Clay | Mark Buckley | 7-6 6-2 | W | H2H | Match data |
| Aug 9, 1985* | Kitzbuhel | ATP 250 | R16 | Clay | Sergio Casal | 3-6 6-7 | L | H2H | Match data |
| Oct 10, 1985* | Brisbane | ATP 250 | R32 | Carpet | Tom Cain | 6-4 2-6 6-3 | W | H2H | Match data |
| Oct 11, 1985* | Brisbane | ATP 250 | R16 | Carpet | Bud Schultz | 6-2 1-6 3-6 | L | H2H | Match data |
| Oct 17, 1985* | Sydney Indoor | ATP 250 | R32 | Hard | Glenn Layendecker | 1-6 7-5 6-2 | W | H2H | Match data |
| Oct 18, 1985* | Sydney Indoor | ATP 250 | R16 | Hard | Andres Gomez | 0-6 2-6 | L | H2H | Match data |
| Oct 24, 1985* | Melbourne Indoor | ATP 250 | R32 | Carpet | Mark Woodforde | 5-7 4-6 | L | H2H | Match data |
| Nov 27, 1985* | Australian Open | Grand Slam | R128 | Grass | Tarik Benhabiles | 6-4 6-4 4-6 6-2 | W | H2H | Match data |
| Nov 29, 1985* | Australian Open | Grand Slam | R64 | Grass | David Pate | 3-6 7-6 6-3 6-0 | W | H2H | Match data |
| Dec 1, 1985* | Australian Open | Grand Slam | R32 | Grass | Tim Gullikson | 4-6 3-6 6-3 4-6 | L | — | Match data |
| Dec 11, 1985* | Sydney Outdoor | ATP 250 | R64 | Grass | Danie Visser | 3-6 6-7 | L | H2H | Match data |
| Dec 19, 1985* | Adelaide | ATP 250 | R32 | Grass | John Frawley | 4-6 6-7 | L | — | Match data |
| Dec 26, 1985* | Melbourne | ATP 250 | R32 | Grass | Peter Doohan | 4-6 4-6 | L | H2H | Match data |
| Apr 10, 1986* | Bari | ATP 250 | R32 | Clay | Thomas Muster | 6-2 6-3 | W | H2H | Match data |
| Apr 11, 1986* | Bari | ATP 250 | R16 | Clay | Lawson Duncan | 3-6 3-6 | L | H2H | Match data |
| May 28, 1986* | Roland Garros | Grand Slam | R128 | Clay | Julio Goes | 4-6 6-3 6-2 6-0 | W | H2H | Match data |
| May 30, 1986* | Roland Garros | Grand Slam | R64 | Clay | Ulf Stenlund | 3-6 1-6 0-6 | L | H2H | Match data |
| Jun 18, 1986* | Bristol | ATP 250 | R64 | Grass | Derrick Rostagno | 7-6 5-7 6-4 | W | H2H | Match data |
| Jun 19, 1986* | Bristol | ATP 250 | R32 | Grass | Todd Witsken | 7-6 6-4 | W | H2H | Match data |
| Jun 20, 1986* | Bristol | ATP 250 | R16 | Grass | Tim Wilkison | 1-6 7-6 5-7 | L | H2H | Match data |
| Jun 25, 1986* | Wimbledon | Grand Slam | R128 | Grass | Tomas Smid | 4-6 3-6 5-7 | L | H2H | Match data |
| Aug 28, 1986* | US Open | Grand Slam | R128 | Hard | Sergio Casal | 1-6 6-3 6-7 2-6 | L | H2H | Match data |
| Oct 16, 1986* | Sydney Indoor | ATP 250 | R32 | Hard | Tomm Warneke | 6-2 6-4 | W | H2H | Match data |
| Oct 17, 1986* | Sydney Indoor | ATP 250 | R16 | Hard | Glenn Layendecker | 5-7 4-6 | L | H2H | Match data |
| Jan 2, 1987* | Adelaide | ATP 250 | R32 | Grass | Johan Carlsson | 7-6 6-7 3-6 | L | H2H | Match data |
| Jan 8, 1987* | Auckland | ATP 250 | R32 | Hard | Mark Woodforde | 1-6 6-3 2-6 | L | H2H | Match data |
| Jan 14, 1987* | Australian Open | Grand Slam | R128 | Grass | Shane Barr | 3-6 4-6 4-6 | L | H2H | Match data |
| Jan 29, 1987* | Sydney Outdoor | ATP 250 | R32 | Grass | Bill Scanlon | 4-6 3-6 | L | H2H | Match data |
| Feb 24, 1987* | Key Biscayne | Masters 1000 | R128 | Hard | Corrado Aprili | 6-3 6-1 6-3 | W | H2H | Match data |
| Feb 25, 1987* | Key Biscayne | Masters 1000 | R64 | Hard | Gilad Bloom | 4-6 6-3 7-5 6-2 | W | H2H | Match data |
| Feb 26, 1987* | Key Biscayne | Masters 1000 | R32 | Hard | Jimmy Connors | 3-6 3-6 1-6 | L | H2H | Match data |
| Mar 19, 1987* | Rotterdam | ATP 250 | R32 | Carpet | Miloslav Mecir | 2-6 3-6 | L | H2H | Match data |
| Mar 26, 1987* | Nancy | ATP 250 | R32 | Carpet | Wally Masur | 6-3 2-6 2-6 | L | H2H | Match data |
| Apr 29, 1987* | Hamburg | ATP 250 | R64 | Clay | Ronald Agenor | 0-6 6-4 7-5 | W | H2H | Match data |
| Apr 30, 1987* | Hamburg | ATP 250 | R32 | Clay | Ivan Lendl | 2-6 1-6 | L | H2H | Match data |
| May 27, 1987* | Roland Garros | Grand Slam | R128 | Clay | Mark Kratzmann | 6-0 6-3 4-6 6-4 | W | H2H | Match data |
| May 29, 1987* | Roland Garros | Grand Slam | R64 | Clay | Michael Robertson | 6-4 7-6 6-3 | W | H2H | Match data |
| May 31, 1987* | Roland Garros | Grand Slam | R32 | Clay | Joakim Nystrom | 4-6 6-7 4-6 | L | H2H | Match data |
| Jun 10, 1987* | Queen's Club | ATP 250 | R64 | Grass | Mel Purcell | 4-6 6-7 | L | H2H | Match data |
| Jul 16, 1987* | Bordeaux | ATP 250 | R32 | Clay | Corrado Aprili | 6-3 3-6 6-1 | W | H2H | Match data |
| Jul 17, 1987* | Bordeaux | ATP 250 | R16 | Clay | Ronald Agenor | 6-7 6-4 3-6 | L | H2H | Match data |
| Aug 5, 1987* | Kitzbuhel | ATP 250 | R64 | Clay | Karel Novacek | 6-3 6-3 | W | H2H | Match data |
| Aug 6, 1987* | Kitzbuhel | ATP 250 | R32 | Clay | Simone Colombo | 6-3 6-3 | W | — | Match data |
| Aug 7, 1987* | Kitzbuhel | ATP 250 | R16 | Clay | Tomas Smid | 6-7 7-6 7-6 | W | H2H | Match data |
| Aug 8, 1987* | Kitzbuhel | ATP 250 | QF | Clay | Ricki Osterthun | 6-3 1-6 7-5 | W | H2H | Match data |
| Aug 8, 1987* | Kitzbuhel | ATP 250 | SF | Clay | Miloslav Mecir | 1-6 2-6 | L | H2H | Match data |
| Aug 27, 1987* | Rye Brook | ATP 250 | R32 | Hard | Dan Goldie | 2-6 2-6 | L | H2H | Match data |
| Sep 3, 1987* | US Open | Grand Slam | R128 | Hard | Michael Kures | 6-2 7-5 6-4 | W | H2H | Match data |
| Sep 5, 1987* | US Open | Grand Slam | R64 | Hard | Ken Flach | 6-1 4-6 6-3 1-6 6-7 | L | H2H | Match data |
| Oct 8, 1987* | Brisbane | ATP 250 | R32 | Hard | Robert Seguso | 6-2 6-7 7-6 | W | H2H | Match data |
| Oct 9, 1987* | Brisbane | ATP 250 | R16 | Hard | Eric Jelen | 4-6 3-6 | L | H2H | Match data |
| Oct 15, 1987* | Sydney Indoor | ATP 250 | R32 | Hard | Broderick Dyke | 6-4 3-6 6-3 | W | H2H | Match data |
| Oct 16, 1987* | Sydney Indoor | ATP 250 | R16 | Hard | Scott Davis | 3-6 6-3 2-6 | L | H2H | Match data |
| Oct 23, 1987* | Tokyo Indoor | ATP 250 | R32 | Carpet | John Ross | 6-1 6-3 | W | — | Match data |
| Oct 24, 1987* | Tokyo Indoor | ATP 250 | R16 | Carpet | Paul Annacone | 4-6 2-6 | L | H2H | Match data |
| Oct 29, 1987* | Hong Kong | ATP 250 | R32 | Hard | Tony Mmoh | 7-6 6-2 | W | H2H | Match data |
| Oct 30, 1987* | Hong Kong | ATP 250 | R16 | Hard | Gary Muller | 6-4 7-6 | W | — | Match data |
| Oct 31, 1987* | Hong Kong | ATP 250 | QF | Hard | John Ross | 6-4 4-6 6-4 | W | — | Match data |
| Oct 31, 1987* | Hong Kong | ATP 250 | SF | Hard | Eliot Teltscher | 5-7 0-6 | L | H2H | Match data |
| Dec 31, 1987* | Adelaide | ATP 250 | R32 | Hard | Patrick Baur | 7-6 5-7 2-6 | L | H2H | Match data |
| Jan 7, 1988* | Sydney Outdoor | ATP 250 | R32 | Grass | Paul Chamberlin | 6-3 4-6 6-3 | W | H2H | Match data |
| Jan 8, 1988* | Sydney Outdoor | ATP 250 | R16 | Grass | Andrew Castle | 7-6 6-3 | W | H2H | Match data |
| Jan 9, 1988* | Sydney Outdoor | ATP 250 | QF | Grass | Andrei Chesnokov | 3-6 5-7 | L | H2H | Match data |
| Jan 13, 1988* | Australian Open | Grand Slam | R128 | Hard | Shane Barr | 6-1 6-3 4-6 6-1 | W | H2H | Match data |
| Jan 15, 1988* | Australian Open | Grand Slam | R64 | Hard | Todd Witsken | 4-6 5-7 2-6 | L | H2H | Match data |
| Feb 11, 1988* | Rotterdam | ATP 250 | R32 | Carpet | Libor Pimek | 4-6 3-6 | L | H2H | Match data |
| Mar 2, 1988* | Indian Wells | Masters 1000 | R64 | Hard | Marian Vajda | 2-6 6-0 6-4 | W | H2H | Match data |
| Mar 3, 1988* | Indian Wells | Masters 1000 | R32 | Hard | Aaron Krickstein | 6-4 6-4 | W | H2H | Match data |
| Mar 5, 1988* | Indian Wells | Masters 1000 | R16 | Hard | Miloslav Mecir | 6-2 0-6 4-6 | L | H2H | Match data |
| Mar 15, 1988* | Key Biscayne | Masters 1000 | R128 | Hard | Tim Wilkison | 7-5 6-4 6-7 6-3 | W | H2H | Match data |
| Mar 16, 1988* | Key Biscayne | Masters 1000 | R64 | Hard | Andrei Chesnokov | 2-6 4-6 6-3 4-6 | L | H2H | Match data |
| Apr 14, 1988* | Nice | ATP 250 | R32 | Clay | Andreas Lesch | 3-6 5-7 | L | H2H | Match data |
| Apr 20, 1988* | Monte Carlo | ATP 250 | R64 | Clay | Alberto Mancini | 6-4 3-6 2-6 | L | H2H | Match data |
| Apr 27, 1988* | Hamburg | ATP 250 | R64 | Clay | Nicklas Kroon | 6-2 6-0 | W | H2H | Match data |
| Apr 28, 1988* | Hamburg | ATP 250 | R32 | Clay | Martin Jaite | 2-6 7-6 6-1 | W | H2H | Match data |
| Apr 29, 1988* | Hamburg | ATP 250 | R16 | Clay | Guillermo Vilas | 3-6 6-4 1-6 | L | H2H | Match data |
| May 5, 1988* | Munich | ATP 250 | R32 | Clay | Hans Schwaier | 6-1 4-6 6-7 | L | H2H | Match data |
| May 25, 1988* | Roland Garros | Grand Slam | R128 | Clay | Eduardo Bengoechea | 7-6 6-7 7-5 2-6 3-6 | L | H2H | Match data |
| Jun 8, 1988* | Queen's Club | ATP 250 | R64 | Grass | Ricardo Acuna | 6-7 6-3 9-7 | W | H2H | Match data |
| Jun 9, 1988* | Queen's Club | ATP 250 | R32 | Grass | Ken Flach | 2-6 7-5 6-3 | W | H2H | Match data |
| Jun 10, 1988* | Queen's Club | ATP 250 | R16 | Grass | Pat Cash | 7-6 6-4 | W | H2H | Match data |
| Jun 11, 1988* | Queen's Club | ATP 250 | QF | Grass | Kevin Curren | 7-5 7-6 | W | H2H | Match data |
| Jun 11, 1988* | Queen's Club | ATP 250 | SF | Grass | Boris Becker | 2-6 4-6 | L | H2H | Match data |
| Jun 22, 1988* | Wimbledon | Grand Slam | R128 | Grass | Gary Muller | 6-7 6-2 6-2 6-0 | W | — | Match data |
| Jun 24, 1988* | Wimbledon | Grand Slam | R64 | Grass | Ivan Lendl | 7-5 2-6 4-6 4-6 | L | H2H | Match data |
| Jul 7, 1988* | Gstaad | ATP 250 | R32 | Clay | Marko Ostoja | 6-4 6-2 | W | H2H | Match data |
| Jul 8, 1988* | Gstaad | ATP 250 | R16 | Clay | Tomas Smid | 6-1 6-4 | W | H2H | Match data |
| Jul 9, 1988* | Gstaad | ATP 250 | QF | Clay | Emilio Sanchez | 4-6 7-6 7-6 | W | H2H | Match data |
| Jul 9, 1988* | Gstaad | ATP 250 | SF | Clay | Horst Skoff | 6-1 6-1 | W | H2H | Match data |
| Jul 10, 1988* | Gstaad | ATP 250 | F | Clay | Jakob Hlasek | 6-3 6-4 7-6 | W | H2H | Match data |
| Jul 13, 1988* | Stuttgart Outdoor | ATP 250 | R64 | Clay | Guillermo Vilas | 6-3 1-6 6-3 | W | H2H | Match data |
| Jul 14, 1988* | Stuttgart Outdoor | ATP 250 | R32 | Clay | Brad Gilbert | 4-6 6-7 | L | H2H | Match data |
| Jul 21, 1988* | Washington | ATP 250 | R32 | Hard | Brian Page | 6-3 6-3 | W | H2H | Match data |
| Jul 22, 1988* | Washington | ATP 250 | R16 | Hard | Chris Pridham | 6-2 6-1 | W | H2H | Match data |
| Jul 23, 1988* | Washington | ATP 250 | QF | Hard | Derrick Rostagno | 4-6 6-7 | L | H2H | Match data |
| Jul 27, 1988* | Stratton Mountain | ATP 250 | R64 | Hard | Kelly Evernden | 6-3 6-0 | W | H2H | Match data |
| Jul 28, 1988* | Stratton Mountain | ATP 250 | R32 | Hard | Dan Cassidy | 6-1 6-2 | W | H2H | Match data |
| Jul 29, 1988* | Stratton Mountain | ATP 250 | R16 | Hard | Michael Robertson | 6-2 6-7 6-2 | W | H2H | Match data |
| Jul 30, 1988* | Stratton Mountain | ATP 250 | QF | Hard | Roger Smith | 6-3 4-6 6-2 | W | H2H | Match data |
| Jul 30, 1988* | Stratton Mountain | ATP 250 | SF | Hard | Paul Annacone | 4-6 3-6 | L | H2H | Match data |
| Aug 17, 1988* | Cincinnati | Masters 1000 | R64 | Hard | Wally Masur | 6-3 3-6 1-6 | L | H2H | Match data |
| Aug 31, 1988* | US Open | Grand Slam | R128 | Hard | Lawson Duncan | 6-0 6-0 6-2 | W | H2H | Match data |
| Sep 2, 1988* | US Open | Grand Slam | R64 | Hard | Boris Becker | 6-3 6-3 6-2 | W | H2H | Match data |
| Sep 4, 1988* | US Open | Grand Slam | R32 | Hard | Marcelo Ingaramo | (w/o) | W | H2H | Match data |
| Sep 7, 1988* | US Open | Grand Slam | R16 | Hard | Martin Laurendeau | 6-4 6-4 6-3 | W | H2H | Match data |
| Sep 9, 1988* | US Open | Grand Slam | QF | Hard | Aaron Krickstein | 6-2 5-7 7-6 5-7 6-3 | W | H2H | Match data |
| Sep 11, 1988* | US Open | Grand Slam | SF | Hard | Mats Wilander | 4-6 4-6 2-6 | L | H2H | Match data |
| Oct 7, 1988* | Brisbane | ATP 250 | R32 | Hard | Shane Barr | 2-6 1-6 | L | H2H | Match data |
| Oct 13, 1988* | Sydney Indoor | ATP 250 | R32 | Hard | Todd Woodbridge | 6-4 6-4 | W | H2H | Match data |
| Oct 14, 1988* | Sydney Indoor | ATP 250 | R16 | Hard | Grant Connell | 6-3 6-7 2-6 | L | H2H | Match data |
| Oct 21, 1988* | Tokyo Indoor | ATP 250 | R32 | Carpet | Shuzo Matsuoka | 6-7 1-6 | L | H2H | Match data |
| Oct 27, 1988* | Paris Indoor | ATP 250 | R32 | Carpet | Aaron Krickstein | 6-7 6-7 | L | H2H | Match data |
| Jan 5, 1989* | Adelaide | ATP 250 | R32 | Hard | Mark Kratzmann | 6-7 1-6 | L | H2H | Match data |
| Jan 12, 1989* | Sydney Outdoor | ATP 250 | R32 | Hard | Carl Uwe Steeb | 3-6 6-4 1-6 | L | H2H | Match data |
| Jan 18, 1989* | Australian Open | Grand Slam | R128 | Hard | Jakob Hlasek | 6-4 6-7 6-3 7-6 | W | H2H | Match data |
| Jan 20, 1989* | Australian Open | Grand Slam | R64 | Hard | Olivier Delaitre | 4-6 6-1 6-1 6-1 | W | H2H | Match data |
| Jan 22, 1989* | Australian Open | Grand Slam | R32 | Hard | Magnus Gustafsson | 7-6 6-0 5-7 2-6 4-6 | L | H2H | Match data |
| Feb 9, 1989* | Rotterdam | ATP 250 | R32 | Carpet | Jorge Lozano | 6-2 6-7 6-3 | W | H2H | Match data |
| Feb 10, 1989* | Rotterdam | ATP 250 | R16 | Carpet | Christian Saceanu | 7-6 7-6 | W | H2H | Match data |
| Feb 11, 1989* | Rotterdam | ATP 250 | QF | Carpet | Marty Davis | 6-3 7-6 | W | H2H | Match data |
| Feb 11, 1989* | Rotterdam | ATP 250 | SF | Carpet | Anders Jarryd | 2-6 4-6 | L | H2H | Match data |
| Mar 2, 1989* | Nancy | ATP 250 | R32 | Hard | Eric Winogradsky | 4-6 6-3 7-6 | W | H2H | Match data |
| Mar 3, 1989* | Nancy | ATP 250 | R16 | Hard | Johan Carlsson | 4-6 1-6 | L | H2H | Match data |
| Mar 15, 1989* | Indian Wells | Masters 1000 | R64 | Hard | Jaime Yzaga | 3-6 6-3 6-1 | W | H2H | Match data |
| Mar 16, 1989* | Indian Wells | Masters 1000 | R32 | Hard | Brad Gilbert | 4-6 4-6 | L | H2H | Match data |
| Mar 21, 1989* | Key Biscayne | Masters 1000 | R128 | Hard | Yahiya Doumbia | 3-6 7-6 6-4 6-2 | W | H2H | Match data |
| Mar 22, 1989* | Key Biscayne | Masters 1000 | R64 | Hard | Brad Drewett | 6-7 6-1 6-3 3-6 6-4 | W | H2H | Match data |
| Mar 23, 1989* | Key Biscayne | Masters 1000 | R32 | Hard | Jim Grabb | 4-6 6-0 6-7 1-6 | L | H2H | Match data |
| May 10, 1989* | Hamburg | ATP 250 | R64 | Clay | Tomas Carbonell | 3-6 3-6 | L | H2H | Match data |
| May 17, 1989* | Rome | Masters 1000 | R64 | Clay | Franco Davin | 1-6 7-5 6-2 | W | H2H | Match data |
| May 18, 1989* | Rome | Masters 1000 | R32 | Clay | Martin Strelba | 6-3 2-6 6-2 | W | H2H | Match data |
| May 20, 1989* | Rome | Masters 1000 | R16 | Clay | Jordi Arrese | 6-3 3-6 5-7 | L | H2H | Match data |
| May 31, 1989* | Roland Garros | Grand Slam | R128 | Clay | Neil Broad | 6-4 6-1 6-4 | W | H2H | Match data |
| Jun 2, 1989* | Roland Garros | Grand Slam | R64 | Clay | Jan Gunnarsson | 5-7 6-3 6-2 7-5 | W | H2H | Match data |
| Jun 4, 1989* | Roland Garros | Grand Slam | R32 | Clay | Ivan Lendl | 6-7 3-6 3-6 | L | H2H | Match data |
| Jun 14, 1989* | Queen's Club | ATP 250 | R64 | Grass | Grant Connell | 5-7 6-2 6-4 | W | H2H | Match data |
| Jun 15, 1989* | Queen's Club | ATP 250 | R32 | Grass | Michael Stich | 6-7 3-6 | L | H2H | Match data |
| Jun 28, 1989* | Wimbledon | Grand Slam | R128 | Grass | John McEnroe | 6-4 6-4 2-6 3-6 6-8 | L | H2H | Match data |
| Jul 27, 1989* | Stuttgart Outdoor | ATP 250 | R32 | Clay | Alex Antonitsch | 4-6 1-6 | L | H2H | Match data |
| Aug 30, 1989* | US Open | Grand Slam | R128 | Hard | Jimmy Brown | 7-5 6-1 6-2 | W | — | Match data |
| Sep 1, 1989* | US Open | Grand Slam | R64 | Hard | Emilio Sanchez | 3-6 7-6 4-6 4-6 | L | H2H | Match data |
| Sep 21, 1989* | Los Angeles | ATP 250 | R32 | Hard | Christo Van Rensburg | 1-6 7-5 6-1 | W | — | Match data |
| Sep 22, 1989* | Los Angeles | ATP 250 | R16 | Hard | Jimmy Arias | 6-3 6-2 | W | H2H | Match data |
| Sep 23, 1989* | Los Angeles | ATP 250 | QF | Hard | Michael Chang | 1-6 3-6 | L | H2H | Match data |
| Sep 28, 1989* | San Francisco | ATP 250 | R32 | Carpet | Anders Jarryd | 1-6 0-6 | L | H2H | Match data |
| Oct 5, 1989* | Brisbane | ATP 250 | R32 | Hard | Peter Doohan | 6-3 6-3 | W | H2H | Match data |
| Oct 6, 1989* | Brisbane | ATP 250 | R16 | Hard | Johan Anderson | 6-3 7-5 | W | H2H | Match data |
| Oct 7, 1989* | Brisbane | ATP 250 | QF | Hard | Todd Woodbridge | 4-6 7-5 4-6 | L | H2H | Match data |
| Oct 12, 1989* | Sydney Indoor | ATP 250 | R32 | Hard | Vijay Amritraj | 6-4 6-0 | W | H2H | Match data |
| Oct 13, 1989* | Sydney Indoor | ATP 250 | R16 | Hard | Nicklas Kroon | 0-6 4-6 | L | H2H | Match data |
| Oct 20, 1989* | Tokyo Indoor | ATP 250 | R32 | Carpet | Richard Matuszewski | 7-6 3-6 6-2 | W | H2H | Match data |
| Oct 21, 1989* | Tokyo Indoor | ATP 250 | R16 | Carpet | Dan Goldie | 7-6 6-4 | W | H2H | Match data |
| Oct 22, 1989* | Tokyo Indoor | ATP 250 | QF | Carpet | Ronald Agenor | 3-6 7-6 6-4 | W | H2H | Match data |
| Oct 22, 1989* | Tokyo Indoor | ATP 250 | SF | Carpet | Carl Uwe Steeb | 4-6 4-6 | L | H2H | Match data |
| Jan 17, 1990* | Australian Open | Grand Slam | R128 | Hard | Andres Gomez | 6-4 3-6 6-1 2-6 3-6 | L | H2H | Match data |
| Feb 14, 1990* | Toronto Indoor | ATP 250 | R64 | Carpet | Jim Courier | 0-6 3-6 | L | H2H | Match data |
| Feb 21, 1990* | Philadelphia | ATP 250 | R64 | Carpet | Michiel Schapers | 7-6 3-6 6-7 | L | H2H | Match data |
| Mar 1, 1990* | Memphis | ATP 250 | R32 | Hard | Tim Wilkison | 6-7 7-6 7-5 | W | H2H | Match data |
| Mar 2, 1990* | Memphis | ATP 250 | R16 | Hard | Glenn Layendecker | 4-6 4-6 | L | H2H | Match data |
| Mar 7, 1990* | Indian Wells Masters | Masters 1000 | R64 | Hard | Andres Gomez | 7-5 6-4 | W | H2H | Match data |
| Mar 8, 1990* | Indian Wells Masters | Masters 1000 | R32 | Hard | Christo Van Rensburg | 6-1 6-3 | W | — | Match data |
| Mar 10, 1990* | Indian Wells Masters | Masters 1000 | R16 | Hard | Jim Courier | 4-6 2-6 | L | H2H | Match data |
| Mar 17, 1990* | Miami Masters | Masters 1000 | R128 | Hard | Mark Kratzmann | 3-6 6-4 3-6 | L | H2H | Match data |
| May 30, 1990* | Roland Garros | Grand Slam | R128 | Clay | Anders Jarryd | 2-6 6-4 1-6 7-6 3-6 | L | H2H | Match data |
| Jun 13, 1990* | Queen's Club | ATP 250 | R64 | Grass | Guillaume Raoux | 6-4 7-6 | W | H2H | Match data |
| Jun 14, 1990* | Queen's Club | ATP 250 | R32 | Grass | Christo Van Rensburg | 3-6 6-7 | L | — | Match data |
| Jun 27, 1990* | Wimbledon | Grand Slam | R128 | Grass | Martin Wostenholme | 6-2 6-2 6-0 | W | H2H | Match data |
| Jun 29, 1990* | Wimbledon | Grand Slam | R64 | Grass | Paul Haarhuis | 5-7 7-5 6-7 6-4 3-6 | L | H2H | Match data |
| Jul 12, 1990* | Newport | ATP 250 | R32 | Grass | Broderick Dyke | 6-3 6-3 | W | H2H | Match data |
| Jul 13, 1990* | Newport | ATP 250 | R16 | Grass | Todd Martin | (w/o) | W | H2H | Match data |
| Jul 14, 1990* | Newport | ATP 250 | QF | Grass | Mark Kratzmann | 6-2 6-4 | W | H2H | Match data |
| Jul 14, 1990* | Newport | ATP 250 | SF | Grass | Eric Jelen | 7-6 6-3 | W | H2H | Match data |
| Jul 15, 1990* | Newport | ATP 250 | F | Grass | Pieter Aldrich | 6-7 6-1 1-6 | L | H2H | Match data |
| Jul 18, 1990* | Washington | ATP 250 | R64 | Hard | Christo Van Rensburg | 6-4 6-0 | W | — | Match data |
| Jul 19, 1990* | Washington | ATP 250 | R32 | Hard | Miguel Nido | 4-6 6-0 6-2 | W | H2H | Match data |
| Jul 20, 1990* | Washington | ATP 250 | R16 | Hard | Richey Reneberg | 4-6 6-2 5-7 | L | H2H | Match data |
| Jul 25, 1990* | Canada Masters | Masters 1000 | R64 | Hard | Alexander Volkov | 5-7 7-5 6-3 | W | H2H | Match data |
| Jul 26, 1990* | Canada Masters | Masters 1000 | R32 | Hard | Brad Pearce | 6-4 6-4 | W | H2H | Match data |
| Jul 28, 1990* | Canada Masters | Masters 1000 | R16 | Hard | Andre Agassi | 2-6 4-6 | L | H2H | Match data |
| Aug 8, 1990* | Cincinnati Masters | Masters 1000 | R64 | Hard | Tim Mayotte | 1-6 6-4 7-5 | W | H2H | Match data |
| Aug 9, 1990* | Cincinnati Masters | Masters 1000 | R32 | Hard | Mats Wilander | 6-3 6-2 | W | H2H | Match data |
| Aug 11, 1990* | Cincinnati Masters | Masters 1000 | R16 | Hard | Andres Gomez | 6-7 3-6 | L | H2H | Match data |
| Aug 15, 1990* | Indianapolis | ATP 250 | R64 | Hard | Scott Davis | 3-6 6-4 6-2 | W | H2H | Match data |
| Aug 16, 1990* | Indianapolis | ATP 250 | R32 | Hard | Jay Berger | 1-6 6-0 5-7 | L | H2H | Match data |