1996-2000 Derby Winners List
* =Derby Record
# =Grand Prize Winner
| Year | Area | Name | Weight | Photo | ||
| 1996 | ||||||
| Bluefish | (shore): | Dennis Williams | 18.47 | |||
| (boat): | Donald Ballou | 18.80 | ||||
| Bonito | (shore): | John Livingston | 9.42 | |||
| (boat): | Perry C. Ambulos | 10.14 | ||||
| Albacore | (shore): | Philip B. Willoughby | 11.68 | # | ||
| (boat): | Arthur N. Vose | 11.97 | ||||
| Bass | (shore): | Marke Plante | 47.37 |  |
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| (boat): | Frank Nuovo | 49.11 | ||||
| Year | Area | Name | Weight | Photo | ||
| 1997 | ||||||
| Bluefish | (shore): | Andre Levesque | 18.97 | |||
| (boat): | Vladimir Smirnov | 18.40 | ||||
| Bonito | (shore): | Stanley Popowitz | 9.49 | # | ||
| (boat): | Joseph Canha | 9.97 | ||||
| Albacore | (shore): | Ken Abbott | 15.38 | |||
| (boat): | Philip Lofgren | 13.26 | ||||
| Bass | (shore): | Dick Hathaway | 50.75 |  |
||
| (boat): | Dick T. Leeson | 40.62 | ||||
| Year | Area | Name | Weight | Photo | ||
| 1998 | ||||||
| Bluefish | (shore): | Abram Williams | 20.58 |  |
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| (boat): | Fred Collins | 16.54 | ||||
| Bonito | (shore): | Bernie Arruda | 7.88 | |||
| (boat): | Christopher Peters | 8.77 | ||||
| Albacore | (shore): | Adam Rose | 12.09 | |||
| (boat): | Walter S. Wlodyka | 14.99 | ||||
| Bass | (shore): | Scott Jadovich | 43.71 | # | ||
| (boat): | Donald Widdiss | 52.41 | ||||
| Year | Area | Name | Weight | Photo | ||
| 1999 | ||||||
| Bluefish | (shore): | Paul B. Schultz | 14.92 | |||
| (boat): | John Cowart | 17.31 | ||||
| Bonito | (shore): | David Desmarais | 10.33 | # | ||
| (boat): | Robert Mocarski | 10.77 | ||||
| Albacore | (shore): | Dave Desmarais | 14.30 | |||
| (boat): | Lev Wlodyka | 12.05 | ||||
| Bass | (shore): | William DeBettencourt | 42.27 |  |
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| (boat): | Jen Clarke | 44.08 |  |
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| Year | Area | Name | Weight | Photo | ||
| 2000 | ||||||
| Bluefish | (shore): | Kevin Hearn | 14.57 | |||
| (boat): | Joe Uva | 19.18 | ||||
| Bonito | (shore): | Eric R. Wolfe | 7.11 | |||
| (boat): | Mark Plante | 10.37 | # |  |
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| Albacore | (shore): | David Skok | 12.96 | |||
| (boat): | John Schillinger | 12.67 | ||||
| Bass | (shore): | Stephen Morris | 41.78 |  |
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| (boat): | Lev Wlodyka | 52.32 | ||||