On 12 August 2014 Bennett joined Bradford City on loan until January. Bennett scored his first goal for the club seven days later, in a 3–1 win away to Crawley Town. Bennett joined Burton Albion on loan in January 2016. On 28 August 2020, Bennett completed a permanent deal to Millwall, signing for an undisclosed fee having spent part of the previous season on loan at the London club. Personal life Bennett was arrested alongside Derby teammate Tom Lawrence in September 2019 on suspicion of drink-driving. Club captain Richard Keogh was injured in the crash, and ruled out for the rest of the 2019–20 season. Derby manager Phillip Cocu said that Keogh felt responsible for the situation, and after Lawrence and Bennett both returned to Derby's team, Cocu said they were "not off the hook". Lawrence and Bennett were then both fined 6 weeks' wages by Derby, and ordered to serve 80 hours of community service and rehabilitation. On 15 October 2019 Lawrence and Bennett pleaded guilty to drink driving at Derby Magistrates Court. International career Bennett represented England at U-16 and U-17 level whilst still only 15, and scored on his debut for the England U-17 side in the Nordic Under-17 Tournament in Iceland in 2011 in a 1–1 draw against Norway U17 in the Group Stages. He grabbed the headlines with his performance in England U-16's 3–1 victory over Northern Ireland U-16's Victory Shield, in which he set up England's opener and then scored two goals in a three-minute second-half spell. He scored another goal in a 4–2 win against Scotland U-16's as England won the Victory Shield. On 17 January 2012, Bennett was called up to the England U-17 squad for the Algarve Tournament in February 2012, joined by his teammate Will Hughes. Bennett appeared in all 3 games, as England won the 3 game tournament with 7 points. Bennett was also called up the 2012 UEFA European Under-17 Football Championship elite round in March 2012, however England failed to qualify for the main tournament, finishing 3rd in their group on 4 points, with their exit confirmed in a 4–0 loss to Spain U17. In August 2012, Bennett was called up to the England U-17 squad for the St George's Park International Tournament, which was played from August–September 2012. Bennett scored the opening goal in Englands 3–2 loss against Italy U-17's as England finished the tournament in