In 1987, Gregory's first season as Saskatchewan's head coach, the Roughriders finished 5–12. Gregory then led the Riders to an 11–7 record in 1988 and a playoff berth. He won the Annis Stukus Trophy as the league's coach of the year. The 2nd-place finish in 1988 finally ended the franchise's 11-year playoff drought, the longest in CFL history. However, the Roughriders were relegated to second place because the Eskimos who had an identical record swept them in the regular season. On November 13, 1988 the Roughriders hosted a playoff game for the first time since 1976, but lost to the BC Lions in the Western Semi-Final by a score of 42–18. Nonetheless, it was a step in the right direction as the Roughriders learned how to win and gained valuable playoff experience that they would need for next season.