 Three weeks later, he scored his second goal in a 2–1 home victory against Hibernian on 24 August.In the second-round of the League Cup, Caballero scored in Dundee's 3–1 victory against Queen of the South on 25 September.Caballero scored a 90th minute winning goal in a 2–1 home victory against Kilmarnock on 5 October.