Brad Gilbert Singles 40 (20–20) Singles 40 (20–20)

| Outcome | Date_ | Championship | Surface | Opponent_in_the_final | Score_in_the_final |
|---|---|---|---|---|---|
| Runner-up | 1989 | Orlando , U.S. | Hard | Andre Agassi | 2–6, 1–6 |
| Winner | 1990 | Rotterdam , Netherlands | Carpet | Jonas Svensson | 6–1, 6–3 |
| Winner | 1990 | Orlando , U.S. | Hard | Christo van Rensburg | 6–2, 6–1 |
| Runner-up | 1990 | Cincinnati , U.S. | Hard | Stefan Edberg | 1–6, 1–6 |
| Winner | 1990 | Brisbane , Australia | Hard | Aaron Krickstein | 6–3, 6–1 |
| Runner-up | 1990 | Grand Slam Cup , Munich | Carpet | Pete Sampras | 3–6, 4–6, 2–6 |
| Runner-up | 1991 | San Francisco , U.S. | Carpet | Darren Cahill | 2–6, 6–3, 4–6 |
| Runner-up | 1991 | Los Angeles , U.S. | Hard | Pete Sampras | 2–6, 7–6 (7–5) , 3–6 |
| Runner-up | 1991 | Sydney Indoor , Australia | Hard (i) | Stefan Edberg | 2–6, 2–6, 2–6 |