Stillman became a regular in the Flames lineup beginning in 1995-96, though it would take a couple seasons for him to begin meeting expectations offensively that he had established in his minor league performances. After scoring only 22 goals and 61 points across his first two seasons, Stillman reached a new level during the 1997-98 season in Calgary, scoring 27 goals. He would match that feat again the following season, and those 27 goals would come to represent his single-season career high. Alas for Stillman , his rounding into form coincided with a downturn in fortune for the Flames. Calgary, who had qualified for the playoffs every season except one between 1976 through until 1996, would not qualify for the playoffs for the rest of his time in the organization. He only played two playoff games for the Flames in 1996, when a declining Flames team qualified as the #7 seed and were swept in the first round by the Blackhawks.