| 23‑Aug‑1993 | Long Island | Hard | R32 | 33 | 3 | (1)Stefan Edberg [SWE] d. Gilbert | 6-3 6-0 | | 0.60 | 0.0% | 8.9% | 48.2% | 51.9% | 34.5% | 4/10 | 1:05 |
| 9‑Aug‑1993 | Cincinnati Masters | Hard | QF | 37 | 3 | (3)Stefan Edberg [SWE] d. Gilbert | 6-4 6-2 | | 0.51 | 6.7% | 6.7% | 50.0% | 63.3% | 46.7% | 1/5 | 1:15 |
| 6‑Apr‑1992 | Tokyo Outdoor | Hard | QF | 20 | 1 | (1)Stefan Edberg [SWE] d. (7)Gilbert | 4-6 6-2 6-3 | | 0.67 | 2.2% | 7.7% | 60.4% | 63.6% | 38.9% | 7/12 | 1:49 |
| 21‑Oct‑1991 | Stockholm Masters | Carpet | R16 | 18 | 1 | (1)Stefan Edberg [SWE] d. (16)Gilbert | 6-2 6-3 | | 0.61 | 6.8% | 0.0% | 57.6% | 67.6% | 40.0% | 6/10 | 1:08 |
| 30‑Sep‑1991 | Sydney Indoor | Hard | F | 25 | 1 | (1)Stefan Edberg [SWE] d. (9)Gilbert | 6-2 6-2 6-2 | | 0.56 | 5.8% | 2.3% | 61.6% | 66.0% | 30.3% | 7/13 | 1:38 |
| 29‑Jul‑1991 | Los Angeles | Hard | SF | 19 | 2 | (4)Gilbert d. (1)Stefan Edberg [SWE] | 7-6(2) 6-7(1) 6-4 | | 1.13 | 8.0% | 3.5% | 54.9% | 75.8% | 58.8% | 6/8 | 2:46 |
| 22‑Oct‑1990 | Stockholm Masters | Carpet | QF | 10 | 1 | (1)Stefan Edberg [SWE] d. (7)Gilbert | 6-4 3-6 6-1 | | | | | | | | | |
| 6‑Aug‑1990 | Cincinnati Masters | Hard | F | 7 | 2 | (1)Stefan Edberg [SWE] d. (4)Gilbert | 6-1 6-1 | (ch) | | | | | | | | |
| 9‑Apr‑1990 | Tokyo Outdoor | Hard | SF | 5 | 2 | (2)Stefan Edberg [SWE] d. (3)Gilbert | 6-1 7-6 | | | | | | | | | |
| 28‑Nov‑1989 | Masters | Carpet | RR | 6 | 3 | Stefan Edberg [SWE] d. Gilbert | 6-1 6-3 | | | | | | | | | |
| 14‑Aug‑1989 | Cincinnati | Hard | F | 9 | 3 | (5)Gilbert d. (2)Stefan Edberg [SWE] | 6-4 2-6 7-6 | | | | | | | | | |
| 28‑Feb‑1989 | Dallas WCT | Carpet | QF | 16 | 5 | Gilbert d. (4)Stefan Edberg [SWE] | 7-6 6-1 6-3 | | | | | | | | | |
| 17‑Aug‑1987 | Cincinnati | Hard | QF | 15 | 3 | (2)Stefan Edberg [SWE] d. (7)Gilbert | 6-1 6-3 | | | | | | | | | |
| 9‑Feb‑1987 | Memphis | Hard | SF | 20 | 2 | (1)Stefan Edberg [SWE] d. (4)Gilbert | 6-4 7-6 | | | | | | | | | |
| 13‑Oct‑1986 | Basel | Hard | SF | 13 | 4 | (1)Stefan Edberg [SWE] d. (3)Gilbert | 7-6 6-2 | | | | | | | | | |
| 3‑Feb‑1986 | Memphis | Carpet | F | 15 | 6 | (8)Gilbert d. (2)Stefan Edberg [SWE] | 7-5 7-6 | | | | | | | | | |
| 23‑Sep‑1985 | San Francisco | Carpet | QF | 18 | 9 | (3)Stefan Edberg [SWE] d. (7)Gilbert | 6-2 6-2 | | | | | | | | | |
| 27‑Aug‑1985 | US Open | Hard | R32 | 20 | 12 | (11)Stefan Edberg [SWE] d. Gilbert | 4-6 6-4 6-1 6-4 | | | | | | | | | |
| 28‑Jan‑1985 | Memphis | Carpet | QF | 27 | 19 | (9)Stefan Edberg [SWE] d. (11)Gilbert | 6-4 6-2 | | | | | | | | | |