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By surface
| Surface | Alessandro Caggiari | Jeff Young |
| Hard |
2 |
3 |
| Clay |
0 |
1 |
All meetings (6)
| Date | Tour | Tournament | Round | Surface | Winner |
Set 1 | Set 2 | Set 3 | Set 4 | Set 5 |
| 2012-01-09 |
WTA |
Hobart |
Semifinal |
Hard |
Yanina Wickmayer |
6-71 |
3-6 |
|
|
|
| 2011-03-07 |
WTA |
Indian Wells |
Quarterfinal |
Hard |
Yanina Wickmayer |
3-6 |
3-6 |
|
|
|
| 2011-02-14 |
WTA |
Dubai |
Round of 16 |
Hard |
Shahar Peer |
6-3 |
4-6 |
1-6 |
|
|
| 2010-02-15 |
WTA |
Dubai |
Round of 64 |
Hard |
Shahar Peer |
6-3 |
2-6 |
5-7 |
|
|
| 2010-01-04 |
WTA |
Auckland |
Semifinal |
Hard |
Yanina Wickmayer |
4-6 |
5-7 |
|
|
|
| 2009-05-04 |
WTA |
Estoril |
Semifinal |
Clay |
Yanina Wickmayer |
0-3 |
|
|
|
|