With his team of Craig Healey, Andrew Lamb, Keith Ives, Daniel Gorman and Tyler Prentice they sailed under cloudy skies in 8-14 knots of breeze against seven other West Coast teams in the double round robin two-day format where each skipper races against one another twice.
That type of format, usually, nicely sorts out who finishes where. But the level of competition this weekend saw not only a tie for first place, but also a tie for third place between Russ Silvestri (USA) and Shane Young (USA) with Silvestri getting the nod for third place and Young getting a fourth-place finish.
"We were pretty lucky the way things broke down," said Bennett. "Shane lost to Russ and Dustin, and we beat Russ and Dusty.
"It takes some luck sometimes, we knew we had to keep winning."
For winning the Long Beach Stop of the California Dreamin' Series, Bennett was awarded the newly created Barney Flam Perpetual Trophy, named after the legendary sailor and 11-time Congressional Cup competitor who recently passed away.
Bennett received the trophy from Flam's son, Steve, who came up with the idea for the trophy to honour his father's memory in tribute to the sport his dad loved and helped to develop.
"The competition was outstanding," said Bennett. "We were match racing here in 2010 and it's gotten better since then. We had great conditions and it was a great regatta."
The California Dreamin' Series is raced in three different venues, San Diego Yacht Club, Jan. 10-11, Long Beach Yacht Club and St. Francis Yacht Club, March 21-22.
This year, the SDYC event didn't happen when the breeze failed to materialize for either of the two days.
That left just the LBYC and St.FYC stops to decide who wins the series and gets an invitation to compete in the 2015 ISAF Grade 2 Ficker Cup at LBYC, May 8-10.
That suits Bennett just fine since as he pointed out, "I didn't make the San Diego event."
Durant sailed exceptionally well, keeping himself in the controlling position over his opponents in most of his races.
"We had a couple of new guys with us that hadn't done a whole lot of match racing," said Durant, "but they picked it up and we were sailing really well. The Long Beach Match Racing Team sailed fine."
This weekend's California Dreamin' Series-Long Beach Stop match race is the first time the ISAF Test Rules have been used in North America.
ISAF International Umpire/International Judge Kirk Brown explains.
"The idea is to make the game simpler," said Brown, "for the sailor to sail, and for the umpires to call.
"To put it simply, the inside boat gets the mark, and all of the old strange exceptions don't apply."
1. Shawn Bennett, San Francisco YC & St. Francis YC, 11 wins, 3 losses
2. Dustin Durant, LBYC, 11, 3 (on tiebreaker)
3. Russ Silvestri, St. FYC, 10, 4
4. Shane Young, LBYC, 10-4 (on tiebreaker)
5. Nicole Breault, St. FYC, 6, 8
6. Dave Hood, LBYC, 4, 10
7. Liz Baylis, SFYC, 3, 11
8. Shala Lawrence, San Diego YC, 1, 13