Dundalk entered the 2018 season as the League Cup holders from 2017, having won that competition and finished as runners-up in both league and FAI Cup. In January the club was taken over by United States-based investors, who had identified the club's European progress as a commercial opportunity. 2018 would turn out to be Stephen Kenny's sixth and final season as manager. He resigned one month after the end of the season to accept the Republic of Ireland U-21 manager's role, and was replaced by his assistant, Vinny Perth for 2019. The 2018 season was Dundalk's 10th consecutive season in the top tier of Irish football, their 83rd in all, and their 92nd in the League of Ireland.