He lives in Kensington, California with his wife, world champion finalist bridge player Sally Woolsey.
He was also runner-up in the 1982 Rosenblum Cup, 1989 Bermuda Bowl and won the Senior Teams at the 2000 World Team Olympiad, and another gold at the 2003 Senior Bowl, as well as more than a dozen American Contract Bridge League (ACBL) North American Bridge Championships (NABC-level) events.
[citation needed] [needs update] Woolsey has written many bridge and backgammon books, and contributed to the bridge bidding theory with innovations including the two-way checkback convention and Woolsey, a defense against opposing notrump openings.
[6] He won the 1978 International Bridge Press Association (IBPA) award for Best Article or Series on a System or Convention.
As of May 2014, the annotated match in the free "Demo issue" is "from 1996 World Cup finals between Malcolm Davis and Kit Woolsey".