He featured for Dundee United in the early rounds of the 2008–09 League Cup, scoring three times against lower league sides. He added to his solitary SPL goal in the latter stages of the 2008–09 season, scoring a last-minute equaliser against Hibernian at Tannadice, then netting again against Hibernian later that season and also against Aberdeen. In September 2009 Goodwillie was arrested after a nightclub doorman was knocked unconscious. Two months later, Goodwillie received a £200 fine for his part in the incident.