Montgomerie is best remembered for captaining Kilmarnock to the Scottish Cup in 1997 – against Falkirk, of all teams. Yet, it is what befell the club in the year he joined the then First Division team from Dumbarton for a £12,000 fee in the summer of 1988 that resonates as Kilmarnock now seek to retain top-flight status that Montgomerie was central to them earning 23 years ago. That promotion success meant all the more because wearying struggles for the club on the pitch and in the boardroom across 1988-89 meant Kilmarnock headed in to the last day of the season needing a miracle to avoid going down to the lowest tier in Scottish football.
In the event of Clyde winning, they required to better their result by five goals. Astonishingly, they looked to have pulled that off with a 6-0 victory away to Queen of the South – only for the efforts of Jim Fleeting’s side to count for nothing when Clyde netted a 94th-minute penalty to win 2-0 at home to St Johnstone.
“I can still see the Kilmarnock scarves lying on the road coming back up that fans had chucked away,” Montgomerie said. “You don’t want to go back to those days. I also remember going to Hibs on the final day of the season when Tommy Burns and Billy Stark were in charge [in May 1994] and going into training one day and Tommy saying to us: ‘Look, if you don’t stay in the Premier League, there will be no full-time football next season’. I know exactly what’s at stake. I wouldn’t like to think it wouldn’t go back to as bad as that, but who knows?