 Having converted two further penalties, one in a victory over Torquay United on 16 August and the other a consolation in a 2–1 defeat to Braintree Town on 13 September, Bailey scored his first goal for Sutton from open play on 8 October when he finished a corner supplied by Ross Stearn in a 4–1 rout of Surrey rivals Woking at Gander Green Lane.On 19 October 2016, it was announced that Bailey had signed a one-year contract extension with Sutton United and will stay with the club until the end of the 2017–18 season.Bailey appeared for Sutton during their historic run to the 5th round of the FA Cup for the first time ever, including a 1–0 victory over Championship club Leeds United on 29 January 2017 and 0–2 defeat to Premier League club Arsenal on 20 February, where he made more tackles and interceptions than any other player.