The team returned to the Olympics in the 1992 Winter Olympics in Albertville, France, but finished poorly. They qualified again for the 1994 Winter Olympics in Lillehammer, Norway. There, the Jamaican four sled stunned many of their critics by finishing in 14th place, ahead of the United States, Russia, Australia, France, and one sled from Italy.

In 2000, the Jamaican bobsleigh team won the gold medal at the World Push Championships in Monaco. At the 2002 Salt Lake City Winter Olympics, the 2-man team of Winston Watt (pilot) and Lascelles Brown (brakeman), set the Park City bobsled track record and the Olympic record for the push-start segment of the 2-man race at 4.78 seconds. Jamaica failed to qualify for the 2006 Winter Olympics in Turin, Italy, or the 2010 Winter Olympics in Vancouver, British Columbia.

After the 2002 Winter Olympics, Lascelles Brown moved to Calgary, Alberta, Canada, where he married his Canadian girlfriend and became a Canadian resident. In 2004, Brown joined the Canadian bobsled team. In 2006, at the Turin Winter Olympics, with his Canadian driver Pierre Lueders, Brown won the Olympic Silver Medal (second place) for the 2-man bobsled event. At the Vancouver Games in 2010, Brown again raced for Canada, and received an Olympic Bronze Medal, when his Canadian 4-man team finished in third place. The successes of Watt and Brown has shown that Jamaica has the ability to produce world-class Winter Olympic athletes, which was one of the premises of the movie Cool Runnings. The real team began at the University of Idaho where Chris Stokes (class of 1987) was on the track team.