Inverness reached the 2017–18 Scottish Challenge Cup Final, after a 3–2 win over Northern Irish invitee side Crusaders at home, meaning the club's would make their fourth cup final appearance, and John Robertson's second challenge cup final at the club. Inverness went on to lift the cup on 24 March 2018, with Carl Tremarco scoring the only goal of the game seconds before the game was due to go into added time. Robertson became the first manager in the cup's history to lift the trophy twice with the same club.