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By surface
| Surface | Jacopo Lomonaco | Josh Osswald |
| Hard |
2 |
0 |
| Clay |
1 |
1 |
All meetings (4)
| Date | Tour | Tournament | Round | Surface | Winner |
Set 1 | Set 2 | Set 3 | Set 4 | Set 5 |
| 2009-08-03 |
WTA |
Los Angeles |
Round of 16 |
Hard |
Maria Sharapova |
6-4 |
0-6 |
3-6 |
|
|
| 2009-05-18 |
WTA |
Warsaw |
Quarterfinal |
Clay |
Alona Bondarenko |
2-6 |
2-6 |
|
|
|
| 2008-04-07 |
WTA |
Amelia Island |
Quarterfinal |
Clay |
Maria Sharapova |
7-69 |
3-6 |
2-6 |
|
|
| 2008-03-10 |
WTA |
Indian Wells |
Round of 16 |
Hard |
Maria Sharapova |
2-6 |
7-5 |
4-6 |
|
|