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During the 1999-2000 we had a fleet high of 19 boats and had 18 boats two other Sundays. The fleet averaged 14 boats over 14 weeks of sailing after getting a late start due to dredging at the Wickford Yacht Club. There were two trophy days. The Ken Payne Memorial Regatta was won by Peter Greene with Chuck Allen second and Tim Dawson third. The Hangover Bowl was won by Tim Dawson with Peter Greene second and Rollin Whyte third. The Flipper Award went to Matt Blanchette Gil Tourgee won the Al Dion Trophy for Race Committee service and was helped during the season by Michelle Wood, Mike Brown, John Smith, and Phil Dion. Thanks also go to the Pleasant Street Wharf and Chris Winsor for the committee and crash boats. Defender Industries provided the trophies. Newport Storm provided the beer for the awards banquet. Thanks for all your help!
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| Place | Name | Points |
| 1 | Peter Greene | 40 |
| 2 | Chuck Allen | 47 |
| 3 | Tim Dawson | 47 |
| 4 | Rollin Whyte | 82 |
| 5 | Bob Hicks | 143 |
| 6 | Dave Sunberg | 149 |
| 7 | Nelson Weiderman | 171 |
| 8 | John Bradley | 172 |
| 9 | Doug Nannig | 173 |
| 10 | Garrett Ianella | 177 |
| 11 | Mike Brown | 186 |
| 12 | Geoff Skog | 216 |
| 13 | Ken Abrams | 259 |
| 14 | Mark Wood | 295 |
| 15 | Matt Blanchette | 345 |
| Sailing, but not qualifying | ||
| Bud Nannig | ||
| Molly Dawson | ||
| Jim Heagney | ||
| Paul Drumm | ||
| Kyle Wilson | ||
| Chris Nannig | ||
| Paul Nannig | ||
| Mark Weiderman | ||
| Good intentions, but not sailing | ||
| Jim Padbury | ||
| Distinguished alumni | ||
| Hans Krezinski | ||