He first took out a licence during the 1951/52 season but it wasn’t until 26 September 1959 that he rode his first winner, Scottish Maid at Market Rasen, for Skegness company director and owner-trainer R W Scott.Dent took out a trainer’s licence in 1962 and went on to train for the next 15 years at various Lincolnshire locations, never staying in the same place for more than three or four years at most. He started out at Keelby, near Grimsby (1962), then moved to Revesby, near Boston (1963-65), Donington-on-Bain, near Louth (1966-67), Hall Stables, Kirton Lindsey, near Gainsborough (1968-71), Fishpond Farm, Ussleby, near Market Rasen (1972-76), and finally at Skipworth Arms Stables, Moortown, near Caistor (1977-78).

Throughout his nomadic training career his string never numbered more than a dozen, mostly horses of the humblest order, thus winners were few and far between. He did, though, train and ride Vital Win to score over hurdles at Uttoxeter on 4 December 1965.

His third and final victory as a jockey came on what was probably the best horse he ever trained, Brass Finisher. Dent saddled him to win hurdle races at Catterick and