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

| Outcome | Date_ | Championship | Surface | Opponent_in_the_final | Score_in_the_final |
|---|---|---|---|---|---|
| Winner | 1988 | Tel Aviv , Israel | Hard | Aaron Krickstein | 4–6, 7–6 (7–5) , 6–2 |
| Runner-up | 1988 | Paris Indoor , France | Carpet | Amos Mansdorf | 3–6, 2–6, 3–6 |
| Winner | 1989 | Memphis , U.S. | Hard (i) | Johan Kriek | 6–2, 6–2, ret. |
| Runner-up | 1989 | Dallas WCT , U.S. | Carpet | John McEnroe | 3–6, 3–6, 6–7 (5–7) |
| Runner-up | 1989 | Washington, D.C. , U.S. | Hard | Tim Mayotte | 6–3, 4–6, 5–7 |
| Winner | 1989 | Stratton Mountain , U.S. | Hard | Jim Pugh | 7–5, 6–0 |
| Winner | 1989 | Livingston , U.S. | Hard | Jason Stoltenberg | 6–4, 6–4 |
| Winner | 1989 | Cincinnati , U.S. | Hard | Stefan Edberg | 6–4, 2–6, 7–6 (7–5) |
| Winner | 1989 | San Francisco , U.S. | Carpet | Anders Järryd | 7–5, 6–2 |