26‑Dec‑1969 | New Orleans | Carpet | F | | | Cliff Richey [USA] d. Osborne | 6-4 6-4 6-2 | | | | | | | | | |
26‑Dec‑1969 | New Orleans | Carpet | SF | | | Osborne d. Peter Curtis [GBR] | 6-3 3-6 6-2 | | | | | | | | | |
26‑Dec‑1969 | New Orleans | Carpet | QF | | | Osborne d. Steve Faulk [USA] | 6-1 6-2 | | | | | | | | | |
21‑Dec‑1969 | Honolulu | | SF | | | Stan Smith [USA] d. Osborne | 12-14 6-4 6-4 | | | | | | | | | |
21‑Dec‑1969 | Honolulu | | R16 | | | Osborne d. Jim Mcmanus [USA] | 4-6 6-1 6-1 | | | | | | | | | |
6‑Oct‑1969 | Las Vegas | Hard | R16 | | | Arthur Ashe [USA] d. Osborne | 6-4 7-5 | | | | | | | | | |
6‑Oct‑1969 | Las Vegas | Hard | R32 | | | Osborne d. Raymond Moore [RSA] | 6-0 6-3 | | | | | | | | | |
29‑Sep‑1969 | Berkeley | Hard | R16 | | | Thomaz Koch [BRA] d. Osborne | 6-4 6-4 | | | | | | | | | |
29‑Sep‑1969 | Berkeley | Hard | R32 | | | Osborne d. Richard Hawkes [NZL] | 6-0 6-3 | | | | | | | | | |
20‑Sep‑1969 | Los Angeles | Hard | SF | | | (10)Richard Gonzalez [USA] d. Osborne | 6-2 7-9 7-5 | | | | | | | | | |
20‑Sep‑1969 | Los Angeles | Hard | QF | | | Osborne d. (4)Arthur Ashe [USA] | 8-6 5-7 6-3 | | | | | | | | | |
20‑Sep‑1969 | Los Angeles | Hard | R16 | | | Osborne d. Roy Barth [USA] | 6-4 5-7 11-9 | | | | | | | | | |
20‑Sep‑1969 | Los Angeles | Hard | R32 | | | Osborne d. (9)Andres Gimeno [ESP] | 1-6 7-5 6-4 | | | | | | | | | |
20‑Sep‑1969 | Los Angeles | Hard | R64 | | | Osborne d. Dick Dell [USA] | 6-3 6-4 | | | | | | | | | |
27‑Aug‑1969 | US Open | Grass | R32 | | | (4)Arthur Ashe [USA] d. Osborne | 5-7 6-4 6-4 6-2 | | | | | | | | | |
27‑Aug‑1969 | US Open | Grass | R64 | | | Osborne d. Premjit Lall [IND] | 4-6 6-3 6-4 7-5 | | | | | | | | | |
27‑Aug‑1969 | US Open | Grass | R128 | | | Osborne d. Peter Burwash [CAN] | 6-2 6-2 6-2 | | | | | | | | | |
16‑Aug‑1969 | Boston | Grass | R32 | | | Roy Barth [USA] d. Osborne | 20-18 6-2 | | | | | | | | | |
16‑Aug‑1969 | Boston | Grass | R64 | | | Osborne d. Dick Crealy [AUS] | 6-3 6-1 | | | | | | | | | |
16‑Aug‑1969 | Boston | Grass | R128 | | | Osborne d. Dave Harmon [USA] | 6-1 6-2 | | | | | | | | | |
11‑Aug‑1969 | Haverford | Grass | R32 | | | Dick Crealy [AUS] d. Osborne | 6-2 6-4 | | | | | | | | | |
11‑Aug‑1969 | Haverford | Grass | R64 | | | Osborne d. Humphrey Hose [VEN] | 6-4 4-6 8-6 | | | | | | | | | |
4‑Aug‑1969 | Southampton | Grass | R64 | | | Bob Mckinley [USA] d. Osborne | 6-4 6-4 | | | | | | | | | |
28‑Jul‑1969 | South Orange | Grass | QF | | | Arthur Ashe [USA] d. Osborne | 6-4 6-4 | | | | | | | | | |
28‑Jul‑1969 | South Orange | Grass | R16 | | | Osborne d. Jaime Pinto Bravo [CHI] | 8-6 6-4 | | | | | | | | | |
28‑Jul‑1969 | South Orange | Grass | R32 | | | Osborne d. F D Robbins [USA] | 7-5 9-7 | | | | | | | | | |
28‑Jul‑1969 | South Orange | Grass | R64 | | | Osborne d. Jean Loup Rouyer [FRA] | 7-5 6-1 | | | | | | | | | |
21‑Jul‑1969 | Indianapolis | Clay | R16 | | | Mike Belkin [CAN] d. (8)Osborne | 7-5 6-4 | | | | | | | | | |
21‑Jul‑1969 | Indianapolis | Clay | R32 | | | (8)Osborne d. Bob Carmichael [AUS] | 6-3 10-8 | | | | | | | | | |
21‑Jul‑1969 | Indianapolis | Clay | R64 | | | (8)Osborne d. Bill Harris [USA] | 6-3 6-4 | | | | | | | | | |
14‑Jul‑1969 | Cincinnati | Clay | R16 | | | (9)Zeljko Franulovic [CRO] d. (6)Osborne | 6-3 7-5 | | | | | | | | | |
14‑Jul‑1969 | Cincinnati | Clay | R32 | | | (6)Osborne d. Bob Carmichael [AUS] | 7-5 7-5 | | | | | | | | | |
14‑Jul‑1969 | Cincinnati | Clay | R64 | | | (6)Osborne d. Jun Kuki [JPN] | 5-7 6-3 6-3 | | | | | | | | | |
14‑Jul‑1969 | Cincinnati | Clay | R128 | | | (6)Osborne d. Terry Bennett [USA] | 6-8 6-4 6-4 | | | | | | | | | |
7‑Jul‑1969 | Washington | Clay | R16 | | | Ismail El Shafei [EGY] d. Osborne | 6-4 6-4 | | | | | | | | | |
7‑Jul‑1969 | Washington | Clay | R32 | | | Osborne d. Patricio Cornejo [CHI] | 6-4 6-2 | | | | | | | | | |
7‑Jul‑1969 | Washington | Clay | R64 | | | Osborne d. Don Candy [AUS] | 6-3 6-1 | | | | | | | | | |
26‑May‑1969 | Sacramento | Hard | QF | | | Alan Fox [USA] d. Osborne | 8-6 6-2 | | | | | | | | | |
26‑May‑1969 | Sacramento | Hard | R16 | | | Osborne d. Rich Anderson [USA] | 6-4 6-2 | | | | | | | | | |
14‑Apr‑1969 | Houston | Clay | R32 | | | Hans Jaochim Plotz [GER] d. Osborne | 6-3 6-1 | | | | | | | | | |
24‑Mar‑1969 | New York | Carpet | R16 | | | Tony Roche [AUS] d. Osborne | 6-3 6-3 | | | | | | | | | |
24‑Mar‑1969 | New York | Carpet | R32 | | | Osborne d. Pancho Segura [ECU] | 6-2 6-3 | | | | | | | | | |
23‑Mar‑1969 | Phoenix | | QF | | | Joaquin Loyo Mayo [MEX] d. Osborne | 6-4 1-6 7-5 | | | | | | | | | |
23‑Mar‑1969 | Phoenix | | R16 | | | Osborne d. Dick Leach [USA] | 6-3 5-7 8-6 | | | | | | | | | |
17‑Feb‑1969 | Macon | Carpet | SF | | | Mark Cox [GBR] d. Osborne | 9-7 1-6 6-3 | | | | | | | | | |
17‑Feb‑1969 | Macon | Carpet | QF | | | Osborne d. Pancho Guzman [ECU] | 6-1 6-4 | | | | | | | | | |
17‑Feb‑1969 | Macon | Carpet | R16 | | | Osborne d. Jan Kukal [CZE] | 11-9 13-11 | | | | | | | | | |
17‑Feb‑1969 | Macon | Carpet | R32 | | | Osborne d. Peter Curtis [GBR] | 4-6 6-2 6-2 | | | | | | | | | |
10‑Feb‑1969 | Salisbury | Hard | R16 | | | Torben Ulrich [DEN] d. Osborne | 6-2 6-3 | | | | | | | | | |
10‑Feb‑1969 | Salisbury | Hard | R32 | | | Osborne d. Richard Russell [JAM] | 6-3 6-3 | | | | | | | | | |