Match Racing

Match RacingOverview

Match racing is a one on one race between two sailboats; typically twice around a windward-leeward course.
Match racing can be seen as a bit more technical than fleet racing, whereas fleet racing is simply a fleet of boats racing around a course. The one vs one match racing requires better boat handling skills, distance judgement, and an enhanced tactical understanding for the rules on the water. Match racing can be super competitive and therefore ends up being very close at the finish line! Oakcliff Sailing Center has the highest concentration of Swedish Match 40s on the planet. These 40 ft boats require 5 or 6 people to sail and sailors from around the world come to Oyster Bay to race on these cutting edge match racing machines! Oakcliff Sailing Center hosts many match racing events in the summer that we can enter. We want to form an all veterans team to get involved and race on these boats against other teams.

Thank you to Oakcliff Sailing Center, Dawn and her team for your support to SailAhead since its very beginning!

Oakcliff Sailing Center
Call SailAhead at (631) 831-8763 for more information on past and future events.

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The who's who of our Match Racing Program:

Dawn RileyDawn Riley

Mentor and so much more!

As CEO and captain of America True, Dawn Riley was the first woman to manage an America’s Cup sailing team. She has raced on four America’s Cup and two Whitbread (now Volvo Ocean Race) teams. Dawn is the former president of the Woman’s Sports Foundation, serves on the board of US Sailing, and is an adviser to several public service organizations.
Dawn currently serves as the Executive Director of Oakcliff Sailing Center.

For more information on Dawn Riley, please visit Dawn's website

Contact Us

32 Greenhills Road
Huntington Station, NY 11746

e: info [at]
p: 631.831.8763

40º52'43.86" N
73º31'03.21" W

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