With Bellerín still working his way back from injury, Maitland-Niles kept his place as Arsenal's starting right-back for the opening games of the 2019–20 Premier League. On 22 September 2019, Maitland-Niles received a red card during the first half of Arsenal's 3–2 victory against Aston Villa at the Emirates Stadium. His sending off came after he received yellow cards in both the 11th and 41st minutes. He scored his first EFL Cup goal against Liverpool in a 5–5 draw (Liverpool won on penalties) at Anfield. On 1 August 2020, Maitland-Niles was selected to start in the FA Cup Final against Chelsea, as Arsenal won their 14th FA Cup.