Dundalk G.N.R. made their debut in the Free State League, the top tier of Irish football, in 1926–27. They had played the previous four seasons in the Leinster Senior League. The team was managed by Joe McCleery, previously of Belfast Celtic F.C., who used his connections to Northern Irish football to ensure a supply of players for the season ahead. Home matches were played at the Dundalk Athletic Grounds (a facility near the town centre shared by several sporting codes), but on weekends when the Athletic Grounds were unavailable, matches would usually move to the Carroll's Recreation Ground.