MidWinter's East Top Five Finishers
| Year | 1st Place | 2nd Place | 3rd Place | 4th Place | 5th Place |
| 1948 | Jack Price | Bud Rust | Bill Buck | Gordon Stager | Bill Prahl |
| 1950 | Hardy Matheson | Bill Matheson | Ding Schoonmaker | Dean McCormick | Bill Prahl |
| 1951 | Ding Schoonmaker | John Hanafourde | Bruce Chadwick | Frank Marquardt | George Kester |
| 1952 | Chet Tingler | Dick Brainard | Howard Boston | Ding Schoonmaker | Frank Marquardt |
| 1953 | Chet Tingler | Dick Brainard | Bill Johnson | Bill Timmis | Jack Wirt |
| 1954 | Frank Greenman | Dick Brainard | Ding Schoonmaker | Chet Tingler | Frank Allcorn |
| 1955 | Bill Mangold | Perrie Ranney | Bill Timmis | Sandy Douglass | Dick Brainard |
| 1956 | Jack Beachem | Dave Minton | Charlie Morgan | Lee Brooks | Bill Nexsen |
| 1957 | Norris Sinclair | Dick Shepard | Ed Walsh | Fred Comlossy | Dave Minton |
| 1958 | Howard Boston | Bill Mangold | Bill Nexsen | John Martin, Jr. | Elmer Richards |
| 1959 | Howard Boston | Doug Westin | Ed Walsh | Jim Hendricksen | Dennis Posey |
| 1960 | Frank Bonsey | Elmer Richards | Chuck Wiley | Ed Walsh | Lou Schowe |
| 1961 | Skip Boston | Elmer Richards | Doug Wake, Jr. | Robert De Rue | Dave Minton |
| 1962 | Ed Sherman | Peter Bordes | Magnus Pedersen | Walt Stubner | Skip Boston |
| 1963 | Walt Stubner | Ed Walsh | Skip Boston | Elmer Richards | Irv Liggett |
| 1964 | Ted Fontelieu | Chuck Wiley | Jack Wanenmacher | Walt Stubner | Skip Boston |
| 1965 | Bruno Markeliunas | Elmer Richards | Jack Wanenmacher | Skip Boston | Richard Percoco |
| 1966 | Ed Walsh | Ed Fontelieu | Peter Barrett | Walt Stubner | Larry Haupt |
| 1967 | Peter Barrett | Skip Boston | Walt Stubner | Ed Sherman | Pete Milnes |
| 1968 | Peter Barrett | Ted Fontelieu | Larry Haupt | Ron Meissner | Pete Milnes |
| 1969 | Rod Glover | Peter Barrett | Dennis Clark | Tom Barnard | Ted Fontelieu |
| 1970 | Ted Fontelieu | Tom Wilson | Irv Liggett | Don Clark | Chuck Steigerwald |
| 1971 | Peter Barrett | Marlin Abramson | Jim Miller | Irv Liggett | Ted Fontelieu |
| 1972 | Chuck Steigerwald | John Foster | Irv Liggett | Chris Pollak | John Greiner |
| 1973 | Jim Miller | Irv Liggett | Larry Haupt | Chuck Steigerwald | Jim Henry |
| 1974 | Mark Gilliland | Marlin Abramson | Ted Fontelieu | Chuck Steigerwald | Bob White |
| 1975 | Tom Dykstra | Bob White | Irv Liggett | Steve Nearing | Ron Rostorfer |
| 1976 | Wally Cross | Bob White | Chuck Steigerwald | Mark Gilliland | Jim Dressell |
| 1977 | Dave Ullman | Rex Gilliland | Jim Dressell | Mark Gilliland | Ted Fontelieu |
| 1978 | Bruce Goldsmith | Chris Pollak | Andy Fox | Champ Glover | Rex Gilliland |
| 1979 | Mark Gilliland | Andy Fox | Dave Ullman | Larry Klein | Chris Pollak |
| 1980 | Ted Fontelieu | Dave Ullman | Greg Fisher | Jack Bauer | Chris Pollak |
| 1981 | Larry Klein | Greg Fisher | Dave Dellenbaugh | Ted Fontelieu | Tim Boucher |
| 1982 | Ched Proctor | Jeff Lenhard | Greg Fisher | Andy Fox | Jim Grundy |
| 1983 | Larry Klein | Ed Baird | Jack Bauer | Jack Finefrock | Mark Ketelson |
| 1984 | Ched Proctor | Greg Fisher | Greg Eiffert | Jack Finefrock | Joe Tomaselli |
| 1985 | Ched Proctor | Greg Fisher | Champ Glover | Jack Finefrock | Wayne Pignolet |
| 1986 | Greg Fisher | Ched Proctor | Jack Finefrock | Elmer Richards | Pete Milnes |
| 1987 | Greg Fisher | Ched Proctor | Jack Finefrock | Elmer Richards | Mark Bramlet |
| 1988 | Greg Fisher | Ched Proctor | Jack Finefrock | Jim Grundy | Lloyd Kitchen, Jr. |
| 1989 | Ched Proctor | Kelson Elam | Greg Fisher | Ed Barbehenn | Larry Liggett |
| 1990 | Greg Fisher | Ched Proctor | Jack Finefrock | Steve Callison | Tom Hubbell |
| 1991 | Greg Fisher | Ched Proctor | Jack Finefrock | Brent Barbehenn | Larry Liggett |
| 1992 | Ched Proctor | Jim Grundy | Bruce King | Jim Graham | David Smedley |
| 1993 | Andy Fox | Bill Draheim | Jack Finefrock | Bryce Dryden | Robbie Brown |
| 1994 | Bryce Dryden | Ched Proctor | Greg Fisher | Serge Vanderhorst | Bill Draheim |
| 1995 | Ched Proctor | Brent Barbehenn | Bruce King | Bob Sessions | Marty Selig |
| 1996 | Bill Draheim | Chris Carroll | Skip Dieball | Brent Barbehenn | Jack Finefrock |
| 1997 | Ched Proctor | Jack Finefrock | Tom Hubbell | Serge Vanderhorst | Mike Gillum |
| 1998 | Ched Proctor | Wayne Pignolet | Dave Hansen | Mike Ingham | Brent Barbehenn |
| 1999 | Greg Fisher | Brent Barbehenn | Paul Abdullah | Robert Bryant | Dave Hansen |
| 2000 | Chris Holzaepfel | Bruce King | Tom Hubbell | Greg Griffin | Dave Hansen |
| 2001 | Bruce King | Barbehenn/Murphy | Champ Glover | Tom Hubbell | Jack Finefrock |
| 2002 | Bill Draheim | Eric Gesner | Bruce King | Skip Dieball | Bob McNitt |
| 2003 | Paul Abdullah | Bill Draheim | Andy McDonald | Dave Hansen | Jack Finefrock |
| 2004 | Skip Dieball | Eric Gesner | Bobby Bryant | Blair Dryden | Brent Barbehenn |
| 2005 | Paul Abdullah | Greg Griffin | Blair Dryden | Lloyd Kitchin | Eric Gesner |
| 2006 | Greg Fisher | Scott Griffin | Greg Griffin | Robby Brown | Eric Gesner |
| 2007 | Greg Fisher | Paul Abdullah | Robby Brown | Greg Griffin | Scott Griffin |
NOTES:
- Regattas in December 1948 through 1953 were held in Miami on Biscayne Bay
- Regattas in 1954 and 1955 were held in Sarasota
- Regattas from 1956 through 2003 were held in St. Petersburg on Tampa Bay
- Data was compiled from BAGPIPES by Elmer Richards
