| MS Regatta | ||||
| Class | Boat Name | Place | Boat Type | Owner |
| 1996 | ||||
| Cruising A | Talaria | 1st | Hinckley 51 | Carney |
| 1998 | ||||
| Class A | Bandito | 1st | N/M 45 | Hale |
| Class C | Ruthless | 3rd | Sabre 38 | Hamlin |
| Cruising A | Talaria | 2nd | Hinckley 51 | Carney |
| Cruising B | Scaramouch | 3rd | Pearson 10 M | Hallett |
| Cruising C | My Pal | 2nd | Pearson 30 | Lowery |
| Multi-hull | Whisperings | 1st | F-27 | Cleary |
| 1999 | ||||
| Class A | Sonnenschein | 3rd | J-35 | Waldron |
| Class C | Synergy | 1st | Farr 38 | Borst |
| Tamarack | 3rd | Farr 36 | Kellogg | |
| Cruising A | Happy Ours | 1st | Ericson 33 | Poirier |
| Cruising B | Wind Game | 1st | Ericson 35 | Reynolds |
| Cruising C | Ajax | 3rd | Ericson 25 | Merrill |
| 2000 | ||||
| Class B | Wisperings | 3rd | F-27 Tri | Cleary |
| Cruising A | Sonnenschein | 3rd | Sabre 38 | Waldron |
| Cruising B | Windgame | 2nd | Ericson 35 | Reynolds |
| Windemere | 3rd | Pearson 32 | Kontos | |
| Cruising C | My Pal | 2nd | Pearson 30 | Lowery |
| 2001 | ||||
| Class B | Kaos | 3rd | G&S | Smithwick |
| Cruising Class A | Osokini | 1st | Catalina 40 | White |
| Cruising Class B | Happy Ours | 1st | Ericson 34 | Poirier |
| The Phoenix | 3rd | Ericson 35 | Greven | |
| Cruising Class C | Robin | 1st | Pearson 30 | Singer |
| 2002 | ||||
| Class A | Bandito | 2nd | N/M 45 | Hale |
| Scaramouche | 3rd | N/M 39 | Hallett | |
| Cruising Class A | The Phoenix | 1st | Ericson 35 | Greven |
| Shamrock | 3rd | Frers 33 | Wellehan | |
| Cruising Class C | Rita P | 1st | Pearson 30 | Rice |
| Robin | 2nd | Pearson 30 | Singer | |
| My Pal | 3rd | Pearson 30 | Lowery | |
| Cruising Class D | Ajax | 1st | Ericson 25 | Merrill |
| 2003 | ||||
| Class A | Scaramouche | 1st | N/M 39 | Hallett |
| Bandito | 3rd | N/M 45 | Hale | |
| Class B | Kaos | 2nd | Frers 36 | Smithwick |
| Class C | Flying J | 1st | J-29 | Dunfey |
| Night Shift | 3rd | Evelyn 36 | Iaconeta | |
| Cruising A | Ruthless | 2nd | Sabre 38 | Hamlin |
| Cruising B | Island Pursuit | 2nd | Pearson 10m | Riley |
| Voodo | 3rd | Kafman | Maloney | |
| Cruising C | Rita P | 2nd | Pearson 30 | Rice |
| Robin | 3rd | Pearson 30 | Singer | |
| Cruising D | Ajax | 1st | Ericson 25 | Merrill |
| The Moe | 2nd | Pearson 26 | Thims | |
| 2004 | ||||
| Class A | Bandito | 2nd | N/M 45 | Hale |
| Class B | Night Shift | 2nd | Evelyn 36 | Iaconeta |
| Snowbird | 3rd | NY 36 | Randall | |
| Class C | Off the Wagon | 2nd | Evelyn 32 | Hallett |
| Multi-hull B | Scout | 2nd | Greeen 38' | Egan |
| Cruising A | Ruthless | 2nd | Sabre 38 | Hamlin |
| Shamrock | 3rd | Frers 33 | Wellehan | |
| Cruising B | Island Pursuit | 3rd | Pearson 10m | Riley |
| Cruising C | Rita P | 1st | Pearson 30 | Rice |
| Cruising E | The Moe | 1st | Pearson 26 | Thims |
| Ajax | 2nd | Ericson 25 | Merrill | |