Outrigger Canoe Club began sponsoring a Hawaii Yacht Racing Association regatta in 1977. The all-class regatta was held in the waters off Waikiki, and drew nearly a hundred boats in classes ranging from Lasers, Cal 20s, Hobie 14s and 16s, Prindles, Rhodes 19s, Tornados, Scorions, Nacras, and Sol Cats, to catamarans and monohulled craft.
The Outrigger Cup was created in 1984 by Sail Committee Chairs Michael Apodaca and Graydon Woolaway as a perpetual trophy for the regatta. In 1984 long-time yacht racing enthusiast and OCC Board of Directors member, Tom Reiner, passed away so the committee decided to create the Outrigger Cup in Reiner’s memory. Woolaway designed the silver bowl and had it engraved. Apodaca designed and hand carved the solid koa wood into its emerald shaped base, adding OCC medallions and sterling silver plates to the uniquely handsome trophy
The Waikiki Yacht Club was the first winner of the Cup on October 14, 1984. It was presented by Reiner’s widow, Sharon.