So did this delay happen? While the publication page says 1989, it's still possible they held back the actual release until January 1990. I do recall having trouble getting a UK Win, Lose or Die from my usual source here in the U.S., The Mysterious Bookshop, who didn't have copies in the summer of 1989.
In fact, I wasn't able to track down a UK Win, Lose or Die until summer of 1990 when I found a copy in Canada. I remember being surprised that I could still find a brand new hardcover on a display table a year after its release. Of course, if it was delayed, this explains that. A delay might also explain why this book is especially hard to find signed.
So I'm throwing out the question to my friends in the UK... Anyone recall exactly when Win, Lose or Die hit bookstore shelves? It would be nice to solve this mystery.
UPDATE: Glidrose over at the CBn forums has found a citation for a review of Win, Lose or Die in the Canadian Globe and Mail on July 22, 1989. So it appears it came out in July '89 as planned.