Match log updated: 2026-08-31 13:51 UTC
Jim Osborne — ATP Match Log
Main draw matches: 239 | W: 118 | L: 121 | Win %: 49.4%
| Opponent | Score | Result | H2H | Match Data | Date ↓ | Round | Tournament | Category | Surface |
|---|---|---|---|---|---|---|---|---|---|
| John Fitzgerald | 4-6 1-6 | L | H2H | Match data | Sep 30, 1982* | R32 | Maui | ATP 250 | Hard |
| Ross Case | 3-6 3-6 | L | H2H | Match data | Oct 2, 1981* | R32 | Maui | ATP 250 | Hard |
| Brian Gottfried | 2-6 3-6 | L | H2H | Match data | Feb 15, 1978* | R64 | Indian Wells Open | ATP 250 | Hard |
| Jim Delaney | 4-6 6-4 5-7 | L | H2H | Match data | Oct 7, 1976* | R32 | Maui | ATP 250 | Hard |
| John Yuill | 4-6 6-4 6-4 | W | H2H | Match data | Oct 6, 1976* | R64 | Maui | ATP 250 | Hard |
| Harold Solomon | 4-6 6-1 5-7 | L | H2H | Match data | Sep 30, 1976* | R32 | San Francisco | ATP 250 | Carpet |
| Billy Martin | 6-4 3-6 6-4 | W | H2H | Match data | Sep 29, 1976* | R64 | San Francisco | ATP 250 | Carpet |
| Harold Solomon | 2-6 4-6 | L | H2H | Match data | Oct 8, 1975* | R32 | Maui | ATP 250 | Hard |
| Roscoe Tanner | 4-6 6-7 | L | H2H | Match data | Oct 10, 1974* | R16 | Maui | ATP 250 | Hard |
| Geoff Masters | 6-3 4-6 6-4 | W | H2H | Match data | Oct 9, 1974* | R32 | Maui | ATP 250 | Hard |
| Vitas Gerulaitis | 4-6 6-3 1-6 | L | H2H | Match data | Mar 29, 1974* | QF | Salt Lake City | ATP 250 | Carpet |
| Jeff Austin | 6-3 6-2 | W | — | Match data | Mar 28, 1974* | R16 | Salt Lake City | ATP 250 | Carpet |
| Jose Higueras | 7-6 7-6 | W | H2H | Match data | Mar 27, 1974* | R32 | Salt Lake City | ATP 250 | Carpet |
| Harold Solomon | 5-7 7-6 4-6 | L | H2H | Match data | Mar 5, 1973 | RR | San Juan | ATP 250 | Hard |
| Thomaz Koch | 6-7 3-6 | L | H2H | Match data | Mar 5, 1973 | RR | San Juan | ATP 250 | Hard |
| Alex Metreveli | 3-6 4-6 | L | — | Match data | Mar 5, 1973 | RR | San Juan | ATP 250 | Hard |
| Onny Parun | 6-7 4-6 | L | H2H | Match data | Mar 5, 1973 | RR | San Juan | ATP 250 | Hard |
| Jaime Fillol | 5-7 6-7 | L | H2H | Match data | Jan 20, 1973* | R16 | Jacksonville | ATP 250 | Hard |
| Billy Higgins | 6-7 6-2 3-6 | L | — | Match data | Sep 20, 1972* | R32 | Seattle | ATP 250 | Carpet |
| Thomaz Koch | 6-7 3-6 | L | H2H | Match data | Sep 5, 1972* | R16 | South Orange | ATP 250 | Hard |
| Torben Ulrich | 6-3 7-6 | W | H2H | Match data | Sep 4, 1972* | R32 | South Orange | ATP 250 | Hard |
| Grover Raz Reid | 4-6 2-6 4-6 | L | H2H | Match data | Sep 1, 1972* | R128 | US Open | Grand Slam | Grass |
| Jairo Velasco | 3-6 7-5 5-7 | L | — | Match data | Aug 17, 1972* | R32 | Canadian Open | ATP 500 | Clay |
| David Brown | 6-1 6-1 | W | — | Match data | Aug 16, 1972* | R64 | Canadian Open | ATP 500 | Clay |
| Vladimir Zednik | 6-7 6-7 | L | H2H | Match data | Aug 12, 1972* | QF | Cleveland | ATP 250 | Carpet |
| Adriano Panatta | 1-6 6-7 | L | H2H | Match data | Aug 9, 1972* | R64 | Indianapolis | ATP 250 | Clay |
| Ian Fletcher | 3-6 6-7 | L | H2H | Match data | Aug 2, 1972* | R32 | Tanglewood | ATP 250 | Clay |
| Jairo Velasco | 3-6 6-2 3-6 | L | — | Match data | Aug 2, 1972* | R64 | Cincinnati Open | ATP 250 | Clay |
| Charlie Owens | 7-5 6-7 4-6 | L | H2H | Match data | Jul 27, 1972* | R16 | Columbus | ATP 250 | Hard |
| Mike Kreiss | 6-3 7-5 | W | H2H | Match data | Jul 26, 1972* | R32 | Columbus | ATP 250 | Hard |
| Buster C Mottram | 4-6 2-6 6-3 6-2 5-7 | L | H2H | Match data | Jun 28, 1972* | R128 | Wimbledon | Grand Slam | Grass |
| John Paish | 9-8 1-6 1-6 | L | H2H | Match data | Jun 26, 1972* | R64 | Queen's Club Championships | ATP 250 | Grass |
| Istvan Gulyas | 1-6 7-5 4-6 6-3 2-6 | L | H2H | Match data | Jun 7, 1972* | R64 | Hamburg Open | ATP 250 | Clay |
| Haroon Rahim | 6-3 3-6 4-6 | L | H2H | Match data | May 10, 1972* | QF | Kansas City | ATP 250 | Hard |
| Stan Smith | 4-6 2-6 | L | H2H | Match data | Mar 11, 1972* | QF | Washington | ATP 250 | Carpet |
| Onny Parun | 6-4 6-3 | W | H2H | Match data | Mar 10, 1972* | R16 | Washington | ATP 250 | Carpet |
| Gerald Battrick | 6-1 6-1 | W | H2H | Match data | Mar 9, 1972* | R32 | Washington | ATP 250 | Carpet |
| Ilie Nastase | 4-6 3-6 | L | H2H | Match data | Mar 8, 1972* | R32 | Hampton | ATP 250 | Hard |
| Stan Smith | 6-3 0-6 4-6 | L | H2H | Match data | Feb 28, 1972 | R16 | New York | ATP 250 | Carpet |
| Ion Tiriac | 6-3 6-3 | W | H2H | Match data | Feb 28, 1972 | R32 | New York | ATP 250 | Carpet |
| Manuel Orantes | 4-6 3-6 | L | H2H | Match data | Feb 23, 1972* | R32 | Salisbury | ATP 250 | Hard |
| Onny Parun | 6-3 6-3 | W | H2H | Match data | Feb 22, 1972* | R64 | Salisbury | ATP 250 | Hard |
| Manuel Orantes | 6-4 6-7 6-7 | L | H2H | Match data | Feb 17, 1972* | R32 | Los Angeles | ATP 250 | Carpet |
| Richard Gonzalez | 4-6 6-7 | L | — | Match data | Feb 11, 1972* | QF | Des Moines | ATP 250 | Carpet |
| Adriano Panatta | 6-7 6-2 6-1 | W | H2H | Match data | Feb 10, 1972* | R16 | Des Moines | ATP 250 | Carpet |
| Ray Ruffels | 7-5 4-6 6-7 | L | H2H | Match data | Sep 30, 1971* | R32 | Berkeley | ATP 250 | Hard |
| Terry Ryan | 7-6 6-2 | W | — | Match data | Sep 29, 1971* | R64 | Berkeley | ATP 250 | Hard |
| John Alexander | 3-6 5-7 | L | H2H | Match data | Sep 23, 1971* | R32 | Los Angeles Open | ATP 250 | Hard |
| Dick Knight | 6-4 7-5 | W | — | Match data | Sep 22, 1971* | R64 | Los Angeles Open | ATP 250 | Hard |
| Georges Goven | 4-6 5-7 | L | H2H | Match data | Sep 20, 1971 | R32 | Sacramento | ATP 250 | Hard |
| Haroon Rahim | 7-6 6-1 | W | H2H | Match data | Sep 20, 1971 | R64 | Sacramento | ATP 250 | Hard |
| Arthur Ashe | 1-6 2-6 6-7 | L | H2H | Match data | Sep 12, 1971* | QF | US Open | Grand Slam | Grass |
| Manuel Orantes | 2-6 6-2 6-2 6-3 | W | H2H | Match data | Sep 10, 1971* | R16 | US Open | Grand Slam | Grass |
| Cliff Richey | 6-7 6-4 6-4 6-4 | W | H2H | Match data | Sep 7, 1971* | R32 | US Open | Grand Slam | Grass |
| Thomaz Koch | 6-3 1-6 6-4 6-3 | W | H2H | Match data | Sep 5, 1971* | R64 | US Open | Grand Slam | Grass |
| Mark Cox | 6-7 7-6 6-7 | L | H2H | Match data | Sep 3, 1971* | R64 | South Orange | ATP 250 | Hard |
| Sammy Giammalva | 4-6 7-6 6-3 6-3 | W | — | Match data | Sep 3, 1971* | R128 | US Open | Grand Slam | Grass |
| Boro Jovanovic | 1-6 2-6 | L | — | Match data | Aug 11, 1971* | R64 | Indianapolis | ATP 250 | Clay |
| Raymond Moore | 4-6 3-6 | L | H2H | Match data | Aug 6, 1971* | QF | Columbus | ATP 250 | Hard |
| Harold Solomon | 4-6 2-6 | L | H2H | Match data | Aug 6, 1971* | R16 | Cincinnati Open | ATP 500 | Clay |
| Clark Graebner | 7-6 6-4 | W | H2H | Match data | Aug 5, 1971* | R16 | Columbus | ATP 250 | Hard |
| Jim Mcmanus | 6-4 7-5 | W | H2H | Match data | Aug 5, 1971* | R32 | Cincinnati Open | ATP 500 | Clay |
| Dick Johnson | 6-1 6-4 | W | — | Match data | Aug 4, 1971* | R32 | Columbus | ATP 250 | Hard |
| Bob Mckinley | 3-6 7-6 6-4 | W | — | Match data | Aug 4, 1971* | R64 | Cincinnati Open | ATP 500 | Clay |
| Jimmy Connors | 5-7 2-6 | L | H2H | Match data | Jul 27, 1971* | R32 | Tanglewood | ATP 250 | Hard |
| Terry Ryan | 7-6 6-4 | W | — | Match data | Jul 26, 1971* | R64 | Tanglewood | ATP 250 | Hard |
| Ken Rosewall | 6-3 6-7 1-6 | L | H2H | Match data | Jul 19, 1971* | R64 | Washington Open | ATP 250 | Clay |
| Phil Dent | (w/o) | L | H2H | Match data | Jun 16, 1971* | R64 | Queen's Club Championships | ATP 250 | Grass |
| Tom Edlefsen | 6-7 4-6 | L | H2H | Match data | May 5, 1971* | QF | Kansas City | ATP 250 | Hard |
| Onny Parun | 1-6 3-6 | L | H2H | Match data | Apr 23, 1971* | R32 | Houston | ATP 250 | Clay |
| Torben Ulrich | 4-6 5-7 | L | H2H | Match data | Apr 21, 1971* | R32 | Charlotte | ATP 250 | Hard |
| Peter Curtis | (w/o) | L | H2H | Match data | Mar 31, 1971* | R32 | San Juan | ATP 250 | Hard |
| Peter Curtis | 3-2 (ret.) | L | H2H | Match data | Feb 25, 1971* | R16 | Salisbury | ATP 250 | Hard |
| Peter Szoke | 7-6 6-3 | W | H2H | Match data | Feb 24, 1971* | R32 | Salisbury | ATP 250 | Hard |
| Zeljko Franulovic | 4-6 4-6 | L | H2H | Match data | Feb 19, 1971* | QF | New York | ATP 250 | Carpet |
| Manuel Santana | 6-4 6-4 | W | H2H | Match data | Feb 18, 1971* | R16 | New York | ATP 250 | Carpet |
| Jaime Fillol | 7-6 6-1 | W | H2H | Match data | Feb 17, 1971* | R32 | New York | ATP 250 | Carpet |
| Haroon Rahim | 0-6 4-6 | L | H2H | Match data | Feb 8, 1971* | R16 | Washington 1 | ATP 250 | Carpet |
| Thomaz Koch | 2-6 4-6 | L | H2H | Match data | Jan 31, 1971* | R16 | Omaha | ATP 250 | Carpet |
| Charlie Pasarell | 4-6 5-6 | L | H2H | Match data | Dec 31, 1970* | QF | New Orleans | ATP 250 | Carpet |
| Stan Smith | 3-6 7-6 1-6 | L | H2H | Match data | Oct 24, 1970* | F | Phoenix | ATP 250 | Hard |
| Barry Mackay | 6-3 6-4 | W | H2H | Match data | Oct 23, 1970* | SF | Phoenix | ATP 250 | Hard |
| Jan Kodes | 3-6 6-3 6-4 | W | H2H | Match data | Oct 23, 1970* | QF | Phoenix | ATP 250 | Hard |
| Ray Ruffels | 6-2 6-3 | W | H2H | Match data | Oct 22, 1970* | R16 | Phoenix | ATP 250 | Hard |
| William Brown | 6-3 1-6 6-1 | W | H2H | Match data | Oct 21, 1970* | R32 | Phoenix | ATP 250 | Hard |
| Bob Carmichael | 5-7 6-7 | L | H2H | Match data | Oct 1, 1970* | R32 | Berkeley | ATP 250 | Hard |
| Lenny Schloss | 7-6 6-3 | W | — | Match data | Sep 30, 1970* | R64 | Berkeley | ATP 250 | Hard |
| Dick Crealy | 4-6 6-3 6-7 | L | H2H | Match data | Sep 21, 1970* | R64 | Los Angeles Open | ATP 250 | Hard |
| Tom Okker | 3-6 2-6 4-6 | L | H2H | Match data | Sep 8, 1970* | R32 | US Open | Grand Slam | Grass |
| Frank Froehling | 7-6 6-3 6-4 | W | H2H | Match data | Sep 6, 1970* | R64 | US Open | Grand Slam | Grass |
| Dick Stockton | 4-6 6-2 4-6 | L | H2H | Match data | Sep 5, 1970* | R16 | South Orange | ATP 250 | Hard |
| Terry Addison | 3-6 6-4 6-2 | W | H2H | Match data | Sep 4, 1970* | R32 | South Orange | ATP 250 | Hard |
| Luis Ayala | 6-7 5-7 6-4 6-3 6-1 | W | H2H | Match data | Sep 4, 1970* | R128 | US Open | Grand Slam | Grass |
| Patricio Cornejo | 6-2 6-4 | W | H2H | Match data | Sep 3, 1970* | R64 | South Orange | ATP 250 | Hard |
| Brian Fairlie | 1-6 2-6 | L | H2H | Match data | Aug 21, 1970* | R16 | Merion | ATP 250 | Grass |
| Roy Barth | 7-5 7-5 | W | H2H | Match data | Aug 20, 1970* | R32 | Merion | ATP 250 | Grass |
| Roscoe Tanner | 7-6 7-5 | W | H2H | Match data | Aug 19, 1970* | R64 | Merion | ATP 250 | Grass |
| Patricio Cornejo | 4-6 9-11 | L | H2H | Match data | Jul 29, 1970* | R64 | Indianapolis | ATP 250 | Clay |
| Patricio Cornejo | 4-6 9-11 | L | H2H | Match data | Jul 29, 1970* | R64 | Indianapolis | ATP 250 | Clay |
| Ilie Nastase | 2-6 4-6 | L | H2H | Match data | Jul 23, 1970* | R32 | Cincinnati Open | ATP 500 | Clay |
| Terry Addison | 5-7 9-7 6-3 | W | H2H | Match data | Jul 22, 1970* | R64 | Cincinnati Open | ATP 500 | Clay |
| Guillermo Vilas | 6-1 2-6 2-6 | L | H2H | Match data | Jul 20, 1970* | R64 | Washington Open | ATP 250 | Hard |
| Peter Curtis | 3-6 3-6 6-1 4-6 | L | H2H | Match data | Jun 24, 1970* | R128 | Wimbledon | Grand Slam | Grass |
| Rod Laver | 3-6 4-6 | L | H2H | Match data | Jun 17, 1970* | R64 | Queen's Club Championships | ATP 250 | Grass |
| Bill Bowrey | 6-8 3-6 | L | H2H | Match data | Jun 11, 1970* | R32 | Bristol | ATP 250 | Grass |
| Barry Mackay | 4-6 4-6 | L | H2H | Match data | May 11, 1970* | R16 | Sacramento | ATP 250 | Hard |
| Arthur Ashe | 4-6 4-6 | L | H2H | Match data | May 6, 1970* | SF | Kansas City | ATP 250 | Hard |
| Tom Edlefsen | 6-4 6-4 | W | H2H | Match data | May 6, 1970* | QF | Kansas City | ATP 250 | Hard |
| Bob Howe | 1-6 10-8 2-6 6-8 | L | — | Match data | May 3, 1970* | R128 | Roland Garros | Grand Slam | Clay |
| Manuel Santana | 3-6 9-11 | L | H2H | Match data | Apr 25, 1970* | R16 | Houston | ATP 250 | Clay |
| Onny Parun | 3-6 6-4 6-3 | W | H2H | Match data | Apr 24, 1970* | R32 | Houston | ATP 250 | Clay |
| Bob Carmichael | 3-6 6-3 4-6 | L | H2H | Match data | Apr 19, 1970* | R16 | Charlotte | ATP 250 | Clay |
| Norm Schellenger | 6-0 6-4 | W | H2H | Match data | Apr 18, 1970* | R32 | Charlotte | ATP 250 | Clay |
| Luis Augusto Garcia | 4-6 5-7 | L | — | Match data | Apr 10, 1970* | R16 | St. Petersburg | ATP 250 | Clay |
| Bob Marcher | 6-0 6-0 | W | — | Match data | Apr 9, 1970* | R32 | St. Petersburg | ATP 250 | Clay |
| Peter Curtis | 6-4 1-6 3-6 | L | H2H | Match data | Mar 31, 1970* | R64 | San Juan | ATP 250 | Hard |
| Juan Gisbert | 7-5 7-9 4-6 | L | — | Match data | Mar 27, 1970* | R16 | Curacao | ATP 250 | Hard |
| Brian Fairlie | 3-6 3-6 | L | H2H | Match data | Mar 19, 1970* | R32 | Barranquilla | ATP 250 | Clay |
| Enrique Quimbaya | 6-0 6-1 | W | — | Match data | Mar 18, 1970* | R64 | Barranquilla | ATP 250 | Clay |
| Jaime Fillol | 5-7 6-4 3-6 | L | H2H | Match data | Mar 14, 1970* | QF | Caracas | ATP 250 | Hard |
| Peter Curtis | 6-1 6-3 | W | H2H | Match data | Mar 13, 1970* | R16 | Caracas | ATP 250 | Hard |
| Richard Russell | 6-1 0-6 8-6 | W | H2H | Match data | Mar 12, 1970* | R32 | Caracas | ATP 250 | Hard |
| Clark Graebner | 1-6 10-12 | L | H2H | Match data | Mar 5, 1970* | R32 | Hampton | ATP 250 | Carpet |
| Zeljko Franulovic | 9-11 6-3 6-8 | L | H2H | Match data | Feb 28, 1970* | R32 | Macon | ATP 250 | Carpet |
| Cliff Richey | 2-6 2-6 | L | H2H | Match data | Feb 20, 1970* | QF | Salisbury | ATP 250 | Hard |
| Peter Curtis | 3-6 6-3 6-3 | W | H2H | Match data | Feb 19, 1970* | R16 | Salisbury | ATP 250 | Hard |
| Jan Kukal | 6-3 6-3 | W | H2H | Match data | Feb 18, 1970* | R32 | Salisbury | ATP 250 | Hard |
| Ian Crookenden | (w/o) | W | H2H | Match data | Feb 17, 1970* | R64 | Salisbury | ATP 250 | Hard |
| John Newcombe | 3-6 8-6 5-7 | L | H2H | Match data | Feb 6, 1970* | R16 | Philadelphia Wct | ATP 250 | Carpet |
| Zeljko Franulovic | 6-8 8-6 8-6 | W | H2H | Match data | Feb 5, 1970* | R32 | Philadelphia Wct | ATP 250 | Carpet |
| Stan Smith | 2-6 5-7 3-6 | L | H2H | Match data | Feb 3, 1970* | F | Omaha | ATP 250 | Hard |
| Thomaz Koch | 8-6 6-2 | W | H2H | Match data | Feb 2, 1970* | SF | Omaha | ATP 250 | Hard |
| Bob Lutz | 6-1 6-2 | W | H2H | Match data | Feb 2, 1970* | QF | Omaha | ATP 250 | Hard |
| Manuel Santana | 23-23 (ret.) | W | H2H | Match data | Feb 1, 1970* | R16 | Omaha | ATP 250 | Hard |
| Cliff Richey | 4-6 4-6 2-6 | L | H2H | Match data | Jan 1, 1970* | F | New Orleans | ATP 250 | Carpet |
| Peter Curtis | 6-3 3-6 6-2 | W | H2H | Match data | Dec 31, 1969* | SF | New Orleans | ATP 250 | Carpet |
| Steve Faulk | 6-1 6-2 | W | H2H | Match data | Dec 31, 1969* | QF | New Orleans | ATP 250 | Carpet |
| Arthur Ashe | 4-6 5-7 | L | H2H | Match data | Oct 10, 1969* | R16 | Las Vegas | ATP 250 | Hard |
| Raymond Moore | 6-0 6-3 | W | H2H | Match data | Oct 9, 1969* | R32 | Las Vegas | ATP 250 | Hard |
| Thomaz Koch | 4-6 4-6 | L | H2H | Match data | Oct 3, 1969* | R16 | Berkeley | ATP 250 | Hard |
| Richard Hawkes | 6-0 6-3 | W | H2H | Match data | Oct 2, 1969* | R32 | Berkeley | ATP 250 | Hard |
| Richard Gonzalez | 2-6 9-7 5-7 | L | — | Match data | Sep 25, 1969* | SF | Los Angeles Open | ATP 250 | Hard |
| Arthur Ashe | 8-6 5-7 6-3 | W | H2H | Match data | Sep 25, 1969* | QF | Los Angeles Open | ATP 250 | Hard |
| Roy Barth | 6-4 5-7 11-9 | W | H2H | Match data | Sep 24, 1969* | R16 | Los Angeles Open | ATP 250 | Hard |
| Andres Gimeno | 1-6 7-5 6-4 | W | H2H | Match data | Sep 23, 1969* | R32 | Los Angeles Open | ATP 250 | Hard |
| Dick Dell | 6-3 6-4 | W | — | Match data | Sep 22, 1969* | R64 | Los Angeles Open | ATP 250 | Hard |
| Arthur Ashe | 7-5 4-6 4-6 2-6 | L | H2H | Match data | Sep 2, 1969* | R32 | US Open | Grand Slam | Grass |
| Premjit Lall | 4-6 6-3 6-4 7-5 | W | H2H | Match data | Aug 31, 1969* | R64 | US Open | Grand Slam | Grass |
| Peter Burwash | 6-2 6-2 6-2 | W | H2H | Match data | Aug 29, 1969* | R128 | US Open | Grand Slam | Grass |
| Roy Barth | 18-20 2-6 | L | H2H | Match data | Aug 20, 1969* | R32 | Boston | ATP 250 | Grass |
| Dick Crealy | 6-3 6-1 | W | H2H | Match data | Aug 18, 1969* | R64 | Boston | ATP 250 | Grass |
| Dave Harmon | 6-1 6-2 | W | — | Match data | Aug 17, 1969* | R128 | Boston | ATP 250 | Grass |
| Dick Crealy | 2-6 4-6 | L | H2H | Match data | Aug 14, 1969* | R32 | Haverford | ATP 250 | Grass |
| Humphrey Hose | 6-4 4-6 8-6 | W | H2H | Match data | Aug 13, 1969* | R64 | Haverford | ATP 250 | Grass |
| Bob Mckinley | 4-6 4-6 | L | — | Match data | Aug 6, 1969* | R64 | Southampton | ATP 250 | Grass |
| Arthur Ashe | 4-6 4-6 | L | H2H | Match data | Aug 2, 1969* | QF | South Orange | ATP 250 | Grass |
| Jaime Pinto Bravo | 8-6 6-4 | W | — | Match data | Aug 1, 1969* | R16 | South Orange | ATP 250 | Grass |
| F D Robbins | 7-5 9-7 | W | H2H | Match data | Jul 31, 1969* | R32 | South Orange | ATP 250 | Grass |
| Jean Loup Rouyer | 7-5 6-1 | W | H2H | Match data | Jul 30, 1969* | R64 | South Orange | ATP 250 | Grass |
| Mike Belkin | 5-7 4-6 | L | H2H | Match data | Jul 25, 1969* | R16 | Indianapolis | ATP 250 | Clay |
| Bob Carmichael | 6-3 10-8 | W | H2H | Match data | Jul 24, 1969* | R32 | Indianapolis | ATP 250 | Clay |
| Bill Harris | 6-3 6-4 | W | — | Match data | Jul 23, 1969* | R64 | Indianapolis | ATP 250 | Clay |
| Zeljko Franulovic | 3-6 5-7 | L | H2H | Match data | Jul 19, 1969* | R16 | Cincinnati Open | ATP 250 | Clay |
| Bob Carmichael | 7-5 7-5 | W | H2H | Match data | Jul 17, 1969* | R32 | Cincinnati Open | ATP 250 | Clay |
| Jun Kuki | 5-7 6-3 6-3 | W | H2H | Match data | Jul 16, 1969* | R64 | Cincinnati Open | ATP 250 | Clay |
| Terry Bennett | 6-8 6-4 6-4 | W | H2H | Match data | Jul 15, 1969* | R128 | Cincinnati Open | ATP 250 | Clay |
| Ismail El Shafei | 4-6 4-6 | L | — | Match data | Jul 11, 1969* | R16 | Washington Open | ATP 250 | Clay |
| Patricio Cornejo | 6-4 6-2 | W | H2H | Match data | Jul 10, 1969* | R32 | Washington Open | ATP 250 | Clay |
| Don Candy | 6-3 6-1 | W | — | Match data | Jul 9, 1969* | R64 | Washington Open | ATP 250 | Clay |
| Alan Fox | 6-8 2-6 | L | — | Match data | May 31, 1969* | QF | Sacramento | ATP 250 | Hard |
| Rich Anderson | 6-4 6-2 | W | — | Match data | May 30, 1969* | R16 | Sacramento | ATP 250 | Hard |
| Hans Joachim Ploetz | 3-6 1-6 | L | H2H | Match data | Apr 17, 1969* | R32 | Houston | ATP 250 | Clay |
| Tony Roche | 3-6 3-6 | L | H2H | Match data | Mar 28, 1969* | R16 | New York | ATP 250 | Carpet |
| Pancho Segura | 6-2 6-3 | W | H2H | Match data | Mar 27, 1969* | R32 | New York | ATP 250 | Carpet |
| Mark Cox | 7-9 6-1 3-6 | L | H2H | Match data | Feb 22, 1969* | SF | Macon | ATP 250 | Carpet |
| Pancho Guzman | 6-1 6-4 | W | — | Match data | Feb 22, 1969* | QF | Macon | ATP 250 | Carpet |
| Jan Kukal | 11-9 13-11 | W | H2H | Match data | Feb 21, 1969* | R16 | Macon | ATP 250 | Carpet |
| Peter Curtis | 4-6 6-2 6-2 | W | H2H | Match data | Feb 20, 1969* | R32 | Macon | ATP 250 | Carpet |
| Torben Ulrich | 2-6 3-6 | L | H2H | Match data | Feb 14, 1969* | R16 | Salisbury | ATP 250 | Hard |
| Richard Russell | 6-3 6-3 | W | H2H | Match data | Feb 13, 1969* | R32 | Salisbury | ATP 250 | Hard |
| Bill Bowrey | 7-9 3-6 | L | H2H | Match data | Dec 13, 1968* | R16 | Brisbane | ATP 250 | Grass |
| Ross Case | 6-3 6-2 | W | H2H | Match data | Dec 12, 1968* | R32 | Brisbane | ATP 250 | Grass |
| Bob Lutz | 2-6 6-3 6-8 10-12 | L | H2H | Match data | Nov 16, 1968* | QF | London 2 | ATP 250 | Hard |
| Onny Parun | 6-4 6-2 5-7 6-2 | W | H2H | Match data | Nov 15, 1968* | R16 | London 2 | ATP 250 | Hard |
| Simon Partridge | 7-5 3-6 6-3 8-6 | W | — | Match data | Nov 14, 1968* | R32 | London 2 | ATP 250 | Hard |
| Tom Leonard | 9-11 6-4 4-6 | L | H2H | Match data | Oct 6, 1968* | R16 | La Jolla | ATP 250 | Hard |
| Bill Yeomans | 6-2 9-7 | W | — | Match data | Oct 5, 1968* | R32 | La Jolla | ATP 250 | Hard |
| Stan Smith | 9-11 6-4 3-6 | L | H2H | Match data | Sep 27, 1968* | QF | Berkeley | ATP 250 | Hard |
| Cliff Mayne | 7-5 6-4 | W | — | Match data | Sep 26, 1968* | R16 | Berkeley | ATP 250 | Hard |
| John Spiegel | 6-3 6-1 | W | — | Match data | Sep 25, 1968* | R32 | Berkeley | ATP 250 | Hard |
| Chris Chapin | 6-4 6-2 | W | — | Match data | Sep 24, 1968* | R64 | Berkeley | ATP 250 | Hard |
| Bob Alloo | 6-3 8-6 | W | — | Match data | Sep 23, 1968* | R128 | Berkeley | ATP 250 | Hard |
| Rod Laver | 2-6 5-7 | L | H2H | Match data | Sep 18, 1968* | R16 | Los Angeles Open | ATP 250 | Hard |
| Clark Graebner | 2-6 5-7 | L | H2H | Match data | Sep 17, 1968* | R16 | Las Vegas | ATP 250 | Hard |
| Cliff Drysdale | 6-4 7-9 6-4 | W | H2H | Match data | Sep 17, 1968* | R32 | Los Angeles Open | ATP 250 | Hard |
| Robert Kreiss | 3-6 6-3 6-4 | W | — | Match data | Sep 16, 1968* | R64 | Los Angeles Open | ATP 250 | Hard |
| Ron Holmberg | 9-11 5-7 9-11 | L | — | Match data | Sep 2, 1968* | R64 | US Open | Grand Slam | Grass |
| Barry Mackay | 8-6 4-6 7-5 6-3 | W | H2H | Match data | Aug 31, 1968* | R128 | US Open | Grand Slam | Grass |
| Peter Curtis | 6-8 2-6 6-3 6-4 11-13 | L | H2H | Match data | Aug 18, 1968* | R128 | Boston 2 | ATP 250 | Grass |
| Clark Graebner | 3-6 6-1 5-7 | L | H2H | Match data | Aug 3, 1968* | SF | South Orange | ATP 250 | Grass |
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.