Newport began the 2018-19 season creditably, securing 23 points from their first 10 games, losing only twice. On 6 January 2019, County won their home FA Cup Third Round tie against Premier League club Leicester City 2–1. The subsequent Fourth Round drew Newport in an away match against Championship club Middlesbrough on 26 January 2019, in which they achieved a 1–1 draw, going on to a home replay victory 2–0 on 5 February 2019. County progressed to the most high-profile fixture in their modern history, the FA Cup Fifth round which they had not reached since 1949. The Exiles were rewarded for their success with a home fixture on against reigning Premier League champions Manchester City on 16 February 2019. County lost the match 4–1 with striker Pádraig Amond scoring a late goal. Amond finished the competition as joint-top scorer with City striker Gabriel Jesus.