 He then moved on to Kilmarnock where he played in seven matches towards the end of the 1988–89 season and scored his first senior goal, although at its conclusion the club were relegated to the third division on goal difference.Stewart moved to second-tier Airdrieonians at the start of the next campaign and began to play regularly.He became an important member of the team in a very eventful period for the "Diamonds", including promotion to the Premier Division in 1991, a 2–1 loss to champions Rangers in the 1992 Scottish Cup Final (in which he was captain with the regular Jimmy Sandison suspended), the club's only European ties against Sparta Prague, relegation in 1993, departure from their stadium in 1994 and relocation to Cumbernauld, victory in the 1994 Scottish Challenge Cup Final, another narrow defeat in the 1995 Scottish Cup Final this time to Celtic, losing four League Cup semi-finals plus a promotion playoff in 1997, and moving to a new home in 1998 - with a win over Celtic in one of the first games there.