
* =Derby Record
# =Grand Prize Winner
| Year | Area | Name | Town | Weight | |
| 1985 | |||||
| Bluefish | (boat): | David Walton | New Bedford, MA | 19.20 | # |
| Bonito | (boat): | Stan Brown and | Doug Kudravetz (tie) | 9.00 | |
| Albacore | (shore): | Harvey Kausel | Slingerlands, NY | 19.15 | |
| Weakfish | (boat): | Sonny Beaulieu | Oak Bluffs | 16.50 | |
| 1986 | |||||
| Bluefish | (boat): | Bill Uniatowski | Oak Bluffs | 19.40 | # |
| Bonito | (shore): | George Kudravetz | Alexandria, VA | 10.95 | |
| Albacore | (shore): | Kevin Hall | West Tisbury | 15.60 | |
| Weakfish | (boat): | Lee Welch | Edgartown | 16.90 | * |
| 1987 | |||||
| Bluefish | (boat): | Amy Musia | Evansville, IN | 17.16 | |
| Bonito | (boat): | Cooper Gilkes III | Edgartwon | 10.19 | # |
| Albacore | (shore): | Keith Lewis | Vineyard Haven | 13.45 | |
| (No Weakfish were caught) | |||||
| 1988 | |||||
| Bluefish | (shore): | Chris MacDonald | Needham, MA | 15.53 | |
| (boat): | Scott Terry | West Tisbury | 17.41 | ||
| Bonito | (shore): | Peter Barobne | Weymouth, MA | 10.84 | |
| (boat): | Paul Bergeron | Oak Bluffs | 8.97 | ||
| Albacore | (shore): | Roger Beach | Edgartown | 15.40 | # |
| (boat): | Pat Drouin | Edgartown | 15.92 | ||
| 1989 | |||||
| Bluefish | (shore): | Sergio Radossi | Ridgefield Park, NJ | 16.07 | |
| (boat): | Michele Rogers | Edgartown | 15.92 | ||
| Bonito | (shore): | Curtis Hopps | Vineyard Haven | 9.89 | # |
| (boat): | Kib Bramhall | West Tisbury | 10.58 | ||
| Albacore | (shore): | Robert Graves | Oak Bluffs | 14.09 | |
| (boat): | Joel Graves | Oak Bluffs | 15.90 | ||
| 1990 | |||||
| Bluefish | (shore): | David Hearn | Burlington, MA | 18.28 | |
| (boat): | Michele Rogers | Edgartown | 18.81 | ||
| Bonito | (shore): | Benjamin Barbee | Weymouth, MA | 9.58 | |
| (boat): | Bryan Abrahamson | Oak Bluffs | 11.22 | * | |
| Albacore | (shore): | Bob Perry | Bridgewater, MA | 14.48 | # |
| (boat): | Don MacGillivray | Vineyard Haven | 19.39 | * |