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USA ATP
7
vs
1
By surface
| Surface | Arthur Ashe | Jim Osborne |
| Hard |
3 |
1 |
| Grass |
3 |
0 |
All meetings (8)
| Date | Tour | Tournament | Round | Surface | Winner |
Set 1 | Set 2 | Set 3 | Set 4 | Set 5 |
| 1971-09-01 |
ATP |
US Open |
Quarterfinal |
Grass |
Arthur Ashe |
6-1 |
6-2 |
7-6 |
|
|
| 1970-05-01 |
ATP |
Kansas City |
Semifinal |
Hard |
Arthur Ashe |
6-4 |
6-4 |
|
|
|
| 1969-10-06 |
ATP |
Las Vegas |
Round of 16 |
Hard |
Arthur Ashe |
6-4 |
7-5 |
|
|
|
| 1969-09-20 |
ATP |
Los Angeles |
Quarterfinal |
Hard |
Jim Osborne |
6-8 |
7-5 |
3-6 |
|
|
| 1969-08-27 |
ATP |
US Open |
Round of 32 |
Grass |
Arthur Ashe |
5-7 |
6-4 |
6-4 |
6-2 |
|
| 1969-07-28 |
ATP |
South Orange |
Quarterfinal |
Grass |
Arthur Ashe |
6-4 |
6-4 |
|
|
|
| 1968-06-10 |
ATP |
Bristol |
Quarterfinal |
— |
Arthur Ashe |
14-12 |
3-6 |
6-4 |
|
|
| 1968-05-29 |
ATP |
Sacramento |
Quarterfinal |
Hard |
Arthur Ashe |
6-3 |
6-4 |
|
|
|