Holders Caley Thistle were eliminated at the first hurdle of the IRN-BRU Cup after going down 2-1 against Dunfermline at Caledonian Stadium.
Inverness made seven changes to the side that had been held to a 0-0 draw by 10-man Ayr United on Saturday, with Jamie McCart, Daniel MacKay and debutant goalkeeper Daniel Hoban among those drafted in.
Dunfermline, who were also much-changed, took the lead from the penalty spot on 24 minutes, when Brad Mckay hauled down Andy Ryan suspiciously close to the edge of the 18-yard box.
Caley Jags improved after the interval, and their equaliser came on 62 minutes when Riccardo Calder’s superb ball in from the left was flicked home by Jordan White for his first Caley Jags goal.
Despite constant pressure in pursuit of a winning goal, Caley Jags were left disappointed when Callum Smith struck the winning goal three minutes from time.
Although Inverness’ defence of the competition ended at the first stage, Ross County booked their place in the second round of the competition, with the Staggies triumphing 2-1 against Hearts colts at Tynecastle.
Co-managers Stuart Kettlewell and Steven Ferguson also named a much-changed side, with goalkeeper Ross Munro and former St Mirren attacker Ross Stewart handed debuts from the start.
Billy Mckay’s first half double put the Dingwall side on their way, with Aidan Keena’s goal just before the interval not enough to prevent County securing their place in Thursday’s draw.