
From 1946 to 1984, with the exception of 1980, the fisherman catching the largest striped bass was the Grand prize winner.
* =Derby Record
# =Grand Prize Winner
| Year | Name | Town | OZ. | ||
| 1946 | Gordon Pitman | New York, N.Y. | 47 | 0 | |
| 1947 | George Marshall | Vineyard Haven | 45 | 13 | |
| 1948 | Al Doyle | Edgartown | 42 | 14 | |
| 1949 | George Marshall | Vineyard Haven | 46 | 14.5 | |
| 1950 | Frank Drake | Vineyard Haven | 40 | 14 | |
| 1951 | Freeman Caswell | Attleboro, MA | 43 | 5 | |
| 1952 | John O. Sylvia | Oak Bluffs | 48 | 1 | |
| 1953 | James Walpole | Edgartown | 51 | 11 | |
| 1954 | Wallace Pinkham | Vineyard Haven | 55 | 9.5 | |
| 1955 | George J. Silva | West Tisbury | 43 | 14 | |
| 1956 | Dick Hathaway | Edgartown | 52 | 9 | |
| 1957 | Ralph Grant | Edgartown | 47 | 8 | |
| 1958 | Oscar Flanders | Chilmark | 51 | 11 | |
| 1959 | Anton Van Breeman | Medford, MA | 50 | 12.5 | |
| 1960 | Philip Baron | Wollaston, MA | 42 | 4 | |
| 1961 | Adam Kurpat | New York, NY | 51 | 14 | |
| 1962 | Harold Benway | Vineyard Haven | 52 | 4 | |
| 1963 | Serge de Somov | Hampton Bay, NY | 52 | 13 | |
| 1964 | Serge de Somov | Hampton Bay, NY | 54 | 14 | |
| 1965 | Serge de Somov | Hampton Bay, NY | 49 | 10 | |
| 1966 | Edward Souza | Lowell, MA | 53 | 15 | |
| 1967 | Fred Kiener | Vineyard Haven | 52 | 6 | |
| 1968 | Robert Rose | Oak Bluffs | 48 | 6 | |
| 1969 | Serge de Somov | Hampton Bay, NY | 51 | 6 | |
| 1970 | Gordon Lingberg | Fairhaven, MA | 42 | 10 | |
| 1971 | Albion Alley | West Tisbury | 49 | 12 | |
| 1972 | Wayne Iacono | Vineyard Haven | 56 | 9 | |
| 1973 | Robert Black | Somerville, MA | 54 | 7.5 | |
| 1974 | Raymond Metcalf | Edgartown | 51 | 14 | |
| 1975 | Roger Silva | West Tisbury | 53 | 14 | |
| 1976 | Rick Connell | Vineyard Haven | 48 | 0 | |
| 1977 | Al Doyle | Edgartown | 56 | 6 | |
| 1978 | Dick Hathaway | Edgartown | 60 | 2 | * |
| 1979 | Dick Hathaway | Edgartown | 55 | 3 | |
| 1980 | Francis Bernard | Oak Bluffs | 49 | 5 | |
| (Bluefish) Lee Welch | Edgartown | 20 | 0 | * | |
| 1981 | Richard Landon | New Haven, CT | 56 | 14 | |
| 1982 | Thomas Bassett | Edgartown | 46.77 | ||
| 1983 | Steve Morris | Oak Bluffs | 49.96 | ||
| 1984 | Jack Coutinho | Vineyard Haven | 48.75 |