Greenock Morton beat Ayr United 5-4 on penalties after a 1-1 draw at Cappielow to book their place in the last 16 of the SPFL Trust Trophy.
Lewis McGregor's opening goal was cancelled out by Josh Mullin for the Honest Men but Dougie Imrie's side progressed on spot-kicks.
There were three red cards in the match - Ayr had Paul Smith sent off before Morton pair Jai Quitongo and Jack Baird were both dismissed.
In Thursday's other third-round tie, Queen of the South thumped FC Edinburgh 4-0 at Palmerston with goals from Connor Murray, David McKay, Michael Ruth and Lee Connelly.
