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Chapman Regatta Past Winners
Sources: Barber of Daily Herald, R. Ponder of Echo, Joe Alfonso, Pete Morrill, Mal Blackwood, BWYC Trophies, PCYC (Sandy), '84 & '91 SRYC (Tom Beery)
| Year | Winner | Host | No of Clubs | No of Boats | Class |
|---|---|---|---|---|---|
| 1950 | Biloxi Yacht Club | 4 | Fishboats | ||
| 1951 | Biloxi Yacht Club | 4 | Fishboats | ||
| 1952 | Pass Christian Yacht Club | 4 | Fishboats | ||
| 1953 | Gulfport Yacht Club | 4 | Fishboats | ||
| 1954 | Biloxi Yacht Club | 4 | Fishboats | ||
| 1955 | Bay Waveland Yacht Club | 4 | Fishboats | ||
| 1956 | Pass Christian Yacht Club | 4 | Fishboats | ||
| 1957 | Gulfport Yacht Club | 4 | Fishboats | ||
| 1958 | Biloxi Yacht Club | 4 | Fishboats | ||
| 1959 | Biloxi Yacht Club | 4 | Fishboats | ||
| 1960 | Biloxi Yacht Club | Bay Waveland Yacht Club | 24 | Fishboats | |
| 1961 | Biloxi Yacht Club | Pass Christian Yacht Club | 24 | Fishboats | |
| 1962 | Gulfport Yacht Club | Gulfport Yacht Club | 24 | Fishboats | |
| 1963 | Biloxi Yacht Club | Biloxi Yacht Club | 24 | Fishboats | |
| 1964 | Biloxi Yacht Club | Bay Waveland Yacht Club | 24 | Fishboats | |
| 1965 | Biloxi Yacht Club | Pass Christian Yacht Club | 24 | Fishboats | |
| 1966 | Biloxi Yacht Club | Gulfport Yacht Club | 24 | Fishboats | |
| 1967 | Biloxi Yacht Club | Gulfport Yacht Club | 24 | Fishboats | |
| 1968 | Biloxi Yacht Club | Biloxi Yacht Club | 24 | Fishboats | |
| 1969 | Pass Christian Yacht Club | Bay Waveland Yacht Club | 12 | Flying Scot | |
| 1970 | Bay Waveland Yacht Club | Pass Christian Yacht Club | 12 | Flying Scot | |
| 1971 | Bay Waveland Yacht Club | Bay Waveland Yacht Club | 20 | Flying Scot | |
| 1972 | Bay Waveland Yacht Club | Pass Christian Yacht Club | 20 | Flying Scot | |
| 1973 | Bay Waveland Yacht Club | Gulfport Yacht Club | 20 | Flying Scot | |
| 1974 | Bay Waveland Yacht Club | Biloxi Yacht Club | 20 | Flying Scot | |
| 1975 | Bay Waveland Yacht Club | Bay Waveland Yacht Club | 20 | Flying Scot | |
| 1976 | Bay Waveland Yacht Club | Pass Christian Yacht Club | 20 | Flying Scot | |
| 1977 | Bay Waveland Yacht Club | Gulfport Yacht Club | 20 | Flying Scot | |
| 1978 | Bay Waveland Yacht Club | Biloxi Yacht Club | 20 | Flying Scot | |
| 1979 | Bay Waveland Yacht Club | Singing River Yacht Club | 20 | Flying Scot | |
| 1980 | Bay Waveland Yacht Club | Bay Waveland Yacht Club | 20 | Flying Scot | |
| 1981 | Bay Waveland Yacht Club | Pass Christian Yacht Club | 20 | Flying Scot | |
| 1982 | Bay Waveland Yacht Club | Gulfport Yacht Club | 20 | Flying Scot | |
| 1983 | Bay Waveland Yacht Club | Biloxi Yacht Club | 7 | 28 | Flying Scot |
| 1984 | Bay Waveland Yacht Club | Singing River Yacht Club | 7 | 28 | Flying Scot |
| 1985 | Bay Waveland Yacht Club | Bay Waveland Yacht Club | 7 | 28 | Flying Scot |
| 1986 | Bay Waveland Yacht Club | Pass Christian Yacht Club | 5 | 20 | Flying Scot |
| 1987 | Pass Christian Yacht Club | Long Beach Yacht Club | 5 | 20 | Flying Scot |
| 1988 | Bay Waveland Yacht Club | Gulfport Yacht Club | 5 | 20 | Flying Scot |
| 1989 | Bay Waveland Yacht Club | Biloxi Yacht Club | 6 | 24 | Flying Scot |
| 1990 | Bay Waveland Yacht Club | Ocean Springs Yacht Club | 7 | 28 | Flying Scot |
| 1991 | Pass Christian Yacht Club | Singing River Yacht Club | 7 | 28 | Flying Scot |
| 1992 | Pass Christian Yacht Club | Bay Waveland Yacht Club | 7 | 28 | Flying Scot |
| 1993 | Pass Christian Yacht Club | Pass Christian Yacht Club | 6 | 24 | Flying Scot |
| 1994 | Bay Waveland Yacht Club | Gulfport Yacht Club | 5 | 20 | Flying Scot |
| 1995 | Gulfport Yacht Club | Gulfport Yacht Club | 6 | 24 | Flying Scot |
| 1996 | Bay Waveland Yacht Club | Biloxi Yacht Club | 15 | Flying Scot | |
| 1997 | Bay Waveland Yacht Club | Ocean Springs Yacht Club | 6 | 17 | Flying Scot |
| 1998 | Bay Waveland Yacht Club | Singing River Yacht Club | 7 | 21 | Flying Scot |
| 1999 | Pass Christian Yacht Club | Bay Waveland Yacht Club | 7 | 19 | Flying Scot |
| 2000 | Pass Christian Yacht Club | Pass Christian Yacht Club | 7 | 18 | Flying Scot |
| 2001 | Pass Christian Yacht Club | Long Beach Yacht Club | 7 | 18 | Flying Scot |
| 2002 | Pass Christian Yacht Club | Gulfport Yacht Club | 4 | 12 | Flying Scot |
| 2003 | Bay Waveland Yacht Club | Biloxi Yacht Club | 5 | 15 | Flying Scot |
| 2004 | Bay Waveland Yacht Club | Ocean Springs Yacht Club | 5 | 15 | Flying Scot |
| 2005 | Pass Christian Yacht club | Bay Waveland Yacht Club | 5 | 15 | Flying Scot |
| 2006 | Pass Christian Yacht Club | Pass Christian Yacht Club | 3 | 9 | Flying Scot |
| 2007 | Bay Waveland Yacht Club | Gulfport Yacht Club | 4 | 12 | Flying Scot |
| 2008 | Pass Christian Yacht Club | Biloxi Yacht Club | 4 | 12 | Flying Scot |
| 2009 | Bay Waveland Yacht Club | Bay Waveland Yacht Club | 6 | 18 | Flying Scot |
| 2010 | Bay Waveland Yacht Club | Pass Christian Yacht Club | 4 | 12 | Flying Scot |
| 2011 | Bay Waveland Yacht Club | Long Beach Yacht Club | 6 | 17 | Flying Scot |
For the events beginning in 1960, BWYC's Leo Seal, PCYC's Rip Terrell, and BYC's Tommy Kemp and Doc Bolton effected a change to make the regatta a 24-boat series, 6 boats/club
For the events beginning in 1969, the Flying Scot replace the Fish Class as the official club-owned boat, so the Chapman Regatta followed suit.
In 1969 change made to allow up to 4 boats/club
In 1996 a change from 4 boats per club to 3 boats per club
Avg. for 51 events, including 10 events with 4 boats and pre-Camille 12-boat years = 18.2 boats/event
| Club | Total number of wins |
| Bay Waveland Yacht Club | 31 |
| Biloxi Yacht Club | 13 |
| Gulfport Yacht Club | 4 |
| Long Beach Yacht Club | |
| Ocean Springs Yacht Club | |
| Pass Christian Yacht Club | 14 |
| Singing River Yacht Club |