[3] Unbeaten in first 11 bouts, he faced Reece Cartwright for the vacant English middleweight title at Walsall Town Hall on 22 September 2018, losing the fight when the ringside doctor ordered it to be stopped in round eight due to facial injuries he had sustained.
[4][5] Denny had a second attempt at winning the title on 30 November 2019, when he took on Linus Udofia at York Hall in London, but again fell short, losing by majority decision with two of the ringside judges scoring the fight 97–94 and 96–94 for his opponent, while the third had it a 94–94 draw.
However, the contest ended in a controversial technical draw when the referee stopped it in the seventh round because of a cut over Wilson-Bent's left eye caused by an accidental clash of heads.
Denny won the fight to finally become English middleweight champion at the fourth time of asking via split decision with two judges giving the bout in his favour 97–93 and 96–93 respectively and the third scoring it 96–94 for Wilson-Bent.
[14] Denny challenged European middleweight champion Matteo Signani at Wolverhampton Civic Hall on 18 November 2023, winning the bout when his opponent failed to answer the bell at the start of round eight.