Kit Woolsey (born Christopher Robin Woolsey in 1943) is an American bridge and backgammon player. He graduated from Oberlin College in 1964. He earned a master's degree in mathematics from the University of Illinois at Urbana-Champaign in 1965.
In bridge, he was the winner of the 1986 Rosenblum Cup world teams championship. 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) national championships. Many of his successes were in partnership with Ed Manfield. He is a World Bridge Federation (WBF) World Grand Master and was inducted into the ACBL Hall of Fame in 2005. In backgammon, he was runner-up in the 1996 World Cup, and is (as of 2007) ranked the #5 backgammon player in the world.
Woolsey authored many bridge and backgammon books, and contributed to the bridge bidding theory with innovations like the two-way checkback convention and a defense system against opposing notrump openings. He won the 1978 International Bridge Press Association (IBPA) award for Best Article or Series on a System or Convention. Since 1984, Woolsey has been one of four (six as of 2005) directors of The Bridge World's Master Solvers Club.
Kit Woolsey is editor of the online backgammon magazine GammonU.