Jamaica at the 1988 Winter Olympics

Jamaica competed in the Winter Olympic Games for the first time at the 1988 Winter Olympics in Calgary, Alberta, Canada. They competed in one sport, Bobsledding, in both the two-man and four-man events and finished outside the medal places in both competitions. Athletes were recruited from the Jamaica Defence Force, which saw Dudley Stokes, Devon Harris, and Michael White become the first members of the team. Caswell Allen was the fourth man, but was injured prior to the start of the Olympics and was replaced by Chris Stokes, who was only in Canada to support his brother and new teammate Dudley.

The two-man event took place first, with Dudley Stokes and White finishing in 30th position overall. American television stations aired footage of the four-man Jamaican team, and despite crashing during the third run and finishing last overall, went on to inspire the 1993 film Cool Runnings.