She began racing sailboats at age 13, and became Commodore of the Sea Scout program at the North Star Sail Club on Lake St. Clair.

She was the pit man in the Defender Series, becoming the first woman to have an active racing role aboard an America's Cup contender.

[6] Riley flew in to Uruguay to take on the skipper duties after Nance Frank stepped down, following a dispute among the team members on the first leg of the race.

Leading by a significant margin going into the last leg, Riley and the Mighty Mary team lost their wind, and Dennis Conner on Stars and Stripes was able to overtake them for the win in the final of the 1995 Citizen's Cup.

[7][8] In 2000 Riley created and led America True, a coed team with a very modest budget that surprised all experts by outracing many of the top teams in individual races of the round robin and Semifinal competitions, including New York Yacht Club's entry and Dennis Conner's Stars & Stripes.

Oakcliff's mission is to improve the sport of sailing in the United States, and it operates out of Oyster Bay, New York with a fleet of nearly fifty racing boats, including the largest collection of Match 40s in the world.