Conway was drafted with the 28th pick of the
2000 MLS SuperDraft by
San Jose Earthquakes. Conway spent his first years as a professional as the backup to
Joe Cannon, but was given his chance at the starting position when Cannon left the Quakes in 2003 for France. In 2000, he went on loan with
Bay Area Seals, playing four games with a 0.50
goals against average. Conway suffered a broken right ankle in preseason and the Quakes were forced to find a replacement; that replacement came in the form of
Canadian international goalkeeper
Pat Onstad from
Rochester Raging Rhinos of the
A-League, who went on to be named Goalkeeper of the year in MLS. Conway remained a capable backup keeper for the Quakes, playing in the occasional
US Open Cup games and when Onstad was injured or away on international duty. Conway has won 2 MLS Cup Championships. After the 2005 season, Conway was traded to the
MetroStars in exchange for a fourth-round draft pick. After the waiving of back-up keeper
Brian Edwards,
Toronto FC acquired the 32-year-old goalkeeper to replace Edwards. Conway made his debut for Toronto in the
Canadian Championship against the
Vancouver Whitecaps May 19, 2010. He continued to make non-league appearances for Toronto throughout the 2010 season within the Canadian Championship and the
CONCACAF Champions League. Conway had a stand out performance versus
Real Salt Lake in the Champions League in a 1–1 home draw on September 28, 2010, setting up teammate
Jacob Peterson with a long throw to start the break. He made his first league appearance for Toronto on October 16, 2010, in a 2–2 home draw versus
Columbus Crew in which he received a red card in the 72nd minute. Toronto traded Conway to
Chicago Fire on January 13, 2011, in exchange for the No. 49 pick in the
2011 MLS SuperDraft. At season's end, Chicago declined his 2012 contract option and he entered the
2011 MLS Re-Entry Draft. Conway was selected by
Los Angeles Galaxy in stage 2 of the draft. However, he instead opted to retire. ==Coaching career==