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. Since 1984, Woolsey has been one of four (before 2005) or six rotating directors of The Bridge World's monthly Master Solvers Club.
Kit Woolsey is editor of the online backgammon magazine GammOnLine. As of May 2014, the annotated match in the free "Demo issue" is "from 1996 World Cup finals between Malcolm Davis and Kit Woolsey".[7]
Kit's wife Sally Woolsey was player-captain of the runner-up team, or losing finalist, for the inaugural, 1994 McConnell Cup[8][9]—a quadrennial world championship event for women that runs to parallel to the open Rosenblum Cup he won in 1986. From 1998 they have played together in all four Mixed Pairs championships at the same convention, now called the World Bridge Series Championships (within the bridge world, World Series for short).[8]
Woolsey, Kit (1982). Matchpoints. Shelbyville, KY: Devyn Press Inc. p. 343. ISBN978-0-910791-00-7. OCLC13491401. — (reprinted 1988 and 1992) Louisville, KY: Devyn Press Inc., pp. 343, OCLC 477153995.
Woolsey, Kit (1980). Partnership Defense in Bridge. Shelbyville, KY: Devyn Press Inc. p. 303. OCLC7498214. — (reprinted 1991), pp. 303, ISBN978-0-910791-68-7.
Woolsey, Kit (1981). Modern Defensive Signalling in Contract Bridge. Port Chester, NY: Barclay Bridge Supplies Inc. p. 64. — (reprinted 1992) Louisville, KY: Devyn Press Inc., pp. 64, ISBN0-910791-40-6.
Baron, Randy; Champney, Ken; Woolsey, Kit (1979). Clobber Their Artificial Club. Shelbyville, NY: Baron Bridge Supplies Inc. p. 20. OCLC69199994. — (reprinted 1980). — (2nd edition 1983), Louisville: Devyn Press Inc., pp. 32. OCLC 10409994. — (reprinted 1990), pp 32.
The Language of Bridge. Bridge winners. 2017
Backgammon
New Ideas in Backgammon (with Hal Heinrich)
How to Play Tournament Backgammon
Backgammon: Master Versus Amateur, Volume 1
MatchQiz Book: Greiner vs Phillip Marmorstein
MatchQiz Book: Hal Heinrich vs. Mika Lidov
MatchQiz Book: Joe Sylvester vs. Nack Ballard
Understanding Backgammon (with Tami Jones)
52 Great Backgammon Tips (with Patti Beadles)
The Backgammon Encyclopedia, Volume 1: Cube Reference Positions
The Backgammon Encyclopedia, Volume 2: More Cube Reference Positions