 Cunliffe made his Fratton Park debut on 6 September 1899 in a friendly match against local rivals Southampton, when he scored the opening goal in a 2–0 victory.Cunliffe scored again in the first Southern League derby match against Southampton at The Dell on 14 April 1900 as Pompey ended their inaugural professional season as runners-up.He also scored Portsmouth's first goal in the FA Cup proper in a 1–1 draw with Blackburn Rovers on 1 February 1900; Portsmouth lost the replay 5–0.