| Monhegan | 2000 | |||
| Class | Boat Name | Place | Boat Type | Owner |
| 1993 | ||||
| Class A Seguin | Scaramouche | 1st | Shaw 32 | Hallett |
| 1994 | ||||
| Class A Seguin | Talaria | 1st | Hinckley 51 | Carney |
| Scaramouche | 2nd | Shaw 32 | Hallett | |
| 1995 | ||||
| Manana | Tamarack | 1st | Evelyn 26 | Kellogg |
| Class A Seguin | Talaria | 1st | Hinckley 51 | Carney |
| Turbo | 3rd | Evelyn 32 | Leary | |
| Double-handed | Happy Ours | 1st | Ericson 33 | Porier |
| 1996 | ||||
| Class A Seguin | Sea Return | 1st | Pearson 53 | Tetrault |
| Talaria | 2nd | Hinckley 51 | Carney | |
| Happy Ours | 3rd | Ericson 33 | Porier | |
| Double-handed | Sea Return | 1st | Pearson 53 | Tetrault |
| Happy Ours | 2nd | Ericson 33 | Porier | |
| 1997 | ||||
| Class A | Shamrock | 3rd | Frers 33 | Wellehan |
| Class A Seguin | Talaria | 1st | Hinckley 51 | Carney |
| Sea Return | 2nd | Pearson 53 | Tetrault | |
| Class B Seguin | Scaramouche | 1st | pearson 10 M | Hallett |
| Double-handed | Sea Return | 1st | Pearson 53 | Tetrault |
| 1998 | ||||
| Class A | Tamarack | 3rd | Farr 37 | Kellogg |
| Class A Seguin | Talaria | 1st | Hinckley 51 | Carney |
| Class B Seguin | My Pal | 2nd | Pearson 30 | Lowery |
| 1999 | ||||
| Class B | Synergy | 2nd | Farr 38 | Borst |
| Tamarack | 3rd | Farr 36 | Kellogg | |
| Class A Seguin | Kaos | 1st | G&S 36 | Smithwick |
| Ruthless | 3rd | Sabre 38 | Hamlin | |
| Class B Seguin | Scaramouche | 1st | Pearson 10M | Hallett |
| Robin | 3rd | Pearson 30 | Singer | |
| Double-handed | Kaos | 1st | ||
| Ruthless | 3rd | |||
| 2000 | ||||
| Overall | Kaos | 1st | G&S 36 | Smithwick |
| Class A | Bandito | 1st | N/M 45 | Hale |
| Class B | Kaos | 1st | G&S 36 | Smithwick |
| Class C- Multi-hull | Scout | 1st | Greene 38 | Egan |
| Manana | Go Dog Go | 1st | J-29 | Ruff |
| Overall Seguin | My Pal | 1st | Pearson 30 | Lowery |
| Class A Seguin | Scaramouche | 1st | Pearson 10 M | Hallett |
| Class B Seguin | My Pal | 1st | Pearson 30 | Lowery |
| Double Handed division | Sonnenschein | 1st | Sabre 38 | Waldron |
| 2001 | ||||
| Class A | Bandito | 3rd | N/M 45 | Hale |
| Manana | Go Dog Go | 2nd | J-29 | Ruff |
| Family Wagon | 3rd | Hallett 27 | Hallett | |
| Cruising Class | Shamrock | 1st | Frers 33 | Wellehan |
| Double Handed | Broken Leash | 2nd | J-35 | Price |
| 2002 | ||||
| Class A | Tamarack | 1st | Dobroth 42' | Kellogg |
| Class B | Kaos | 2nd | Frers 36' | Smithwick |
| Manana | Go Dog Go | 1st | J-29 | Ruff |
| Double-handed racing | Broken Leash | 1st | J-35 | Price |
| Off the Wagon | 2nd | Evelyn 32 | Hallett | |
| 2003 | ||||
| Class A | Scaramouche | 2nd | N/M 39 | Hallett |
| Class B | Kaos | 1st | Frers 36' | Smithwick |
| Double Handed Sequin | Rita P | 1st | Pearson 30 | Rice |
| Double handed racing | Broken Leash | 1st | J-35 | Price |
| Flying J | 2nd | J-29 | Dunfey | |
| 2004 | ||||
| Class B | Kaos | 1st | Frers 41 | Smithwick |
| Beausoleil | 2nd | Beneteau 45 | Parent | |
| Tamarack | 3rd | Dobroth 42' | Kellogg | |
| Class B Seguin | The Phoenix | 1st | Ericson 38 | Greven |
| Double Handed Sequin | Rita P | 2nd | Pearson 30 | Rice |