Drury has previously played for Manchester City, Burton Albion and St Mirren, Bristol Rovers, Gainsborough Trinity and Grimsby Borough.
[7] Drury made his debut for Burton Albion in the FA Cup 3rd round playing 73 minutes in a 2–0 away defeat against Leicester City at King Power Stadium.
[14] Drury had been training with Peterborough United with a view to signing a year-long deal,[15] however, on 19 August 2014, it was announced that he would spend the next season on loan with St Mirren in the Scottish Premiership.
[17] Drury scored his first league goal of the campaign in the fourth game for St Mirren, an equaliser in the 2–1 away defeat against Kilmarnock on 23 September 2014, stabbing the ball home from close range.
[19] On 5 January St Mirren announced that Drury had left the club, cutting short his one-year loan period from Manchester City.
[26] He then spent a few days on trial at Rotherham United[27] before signing non-contractual (dual registration) terms for National League North side Gainsborough Trinity on 4 November 2015.
[33] On 22 March 2016, he scored an equalising goal on 60 minutes in a 1–2 home defeat over Tadcaster Albion in the Northern Counties East League Cup.
[35] Drury started the 2016–17 season at right-back, he provided two assists in the 3–2 home victory over Ollerton Town on 6 August 2016, his performance that day awarding him man of the match.