Ranford won his first Stanley Cup in 1988, as the backup to Grant Fuhr. However, in 1990 despite constant comparisons to the injured Fuhr, Ranford emerged as a first-rate goaltender, leading the Oilers to the Stanley Cup and winning the Conn Smythe Trophy (playoff MVP) in the process. It was the last cup that the Edmonton Oilers dynasty would win. Ranford went on to play the next six seasons in Edmonton, before being dealt back to the Boston Bruins on January 11, 1996 for Mariusz Czerkawski, Sean Brown, and a 1st Round Pick in the 1996 Entry Draft (Matthieu Descoteaux).