On 31 August 2016, he joined Coventry City on loan until January. Sterry scored his first goal for Coventry in an FA Cup tie against Morecambe on 6 November 2016.
On 31 January 2018, Sterry joined Crewe Alexandra on loan until the end of the season. He made his Crewe debut on 3 February 2018 at Notts County.
