| Pilot Race | www.portlandyachtclub.com | |||
| Class | Boat Name | Place | Boat Type | Owner |
| 1999 | ||||
| Class A | Bandito | 2nd | N/M 45 | Hale |
| Class B | Synergy | 2nd | Farr 38 | Borst |
| 2000 | ||||
| Class A | Bandito | 1st | N/M 45 | Hale |
| Class B | Synergy | 2nd | Farr 37 | Borst |
| Go Dog Go | 3rd | J-29 | Ruff | |
| Cruising Class | Rita P | 2nd | Pearson 30 | Rice |
| 2001 | ||||
| Class A | Bandito | 1st | N/M 45 | Hale |
| Class B | Kaos | 1st | G&S 36 | Smithwick |
| Class C | Go Dog Go | 1st | J-29 | Ruff |
| Family Wagon | 2nd | Hallett 27 | Hallett | |
| 2002 | ||||
| Class A | Bandito | 1st | N/M 45 | Hale |
| Class B | Kaos | 3rd | Frers 36 | Smithwick |
| 2003 | ||||
| Class A | Scaramouche | 1st | N/M 39 | Hallett |
| Tamarack | 2nd | Dobroth 42 | Kellogg | |
| Bandito | 3rd | N/M 45 | Hale | |
| Class B | Go Dog Go | 1st | J-29 | Ruff |
| Kaos | 3rd | Frers 36 | Smithwick | |
| Cruising Class | Rita P | 3rd | Pearson 30 | Rice |
| 2004 | ||||
| Class A | Scaramouche | 1st | N/M 39 | Hallett |
| Revolution | 2nd | Farr 43 | Rogers | |
| Cruising Class | Rita P | 2nd | Pearson 30 | Rice |
| My Pal | 3rd | Pearson 30 | Lowery |