In the 2014–15 season, "The Ports" signed Linfield playmaker Robert Garrett, "Blues" captain Michael Gault and reliable "Blues" striker Mark McAilaster. This had meant a lot was expected of the club to challenge for the title and they started the season with an impressive 3–0 win over Warren Feeney's Linfield and several wins over Glenavon and eventual champions Crusaders They also showed the capability of being champions when in a match against basement side Institute; with the match leveled at 1–1 in the dying minutes, Michael Gault scored a late, long distance effort to secure the three points amid the sense of relief for all those at the match. However, a shock 2–1 defeat away to Warrenpoint Town saw "The Ports" blow a chance to go seven points clear in the NIFL Premiership, and losing 3–2 to the Linfield, with Ross Redman missing a penalty in the final minute of the match. This saw "The Ports" fall away in the league, but in the Irish Cup quarter-final, they took on Linfield once again at Shamrock Park, with Chris Casement putting the home side 1–0 up with a penalty very early on, and a superb performance from Scot Gary Twigg pitching in with a simple finish after a mistake from Linfield defender Glenn Belezika and a magnificent first-time finish had meant Portadown were 3–0 up after about 30 minutes. They went on to win the match 3–2 with a huge home crowd staying well after the final whistle to show their appreciation.