By surface
| Surface | Jimmy Connors | Greg Holmes |
|---|---|---|
| Hard | 1 | 2 |
All meetings (3)
| Date | Tour | Tournament | Round | Surface | Winner | Set 1 | Set 2 | Set 3 | Set 4 | Set 5 |
|---|---|---|---|---|---|---|---|---|---|---|
| 1987-08-03 | ATP | Stratton Mountain | Round of 64 | Hard | Greg Holmes | 5-7 | 5-7 | |||
| 1987-03-16 | ATP | Orlando | Round of 16 | Hard | Jimmy Connors | 6-2 | 7-6 | |||
| 1985-02-18 | ATP | La Quinta | Quarterfinal | Hard | Greg Holmes | 0-6 | 3-6 |