The 2019-20 campaign delivered a competitive, though ultimately heartbreaking, season for Portsmouth as Pompey finished 5th in League One, securing a play-off spot in a season curtailed by the COVID-19 pandemic. Leading the charge was the exciting Republic of Ireland international Ronan Curtis, whose 11 league goals (and a total of 14, matching John Marquis) powered a side that also reached the EFL Trophy final and the FA Cup Fifth Round against Arsenal. Despite their strong league finish under manager Kenny Jackett, the season was defined by the agony of a penalty-shootout defeat to Oxford United in the play-off semi-finals, marking a painful end to a campaign built on renewed promotion ambition.