At Nottingham Forest, Bowles failed to settle under the management of Brian Clough and he ruled himself out of the 1980 European Cup Final after Clough refused to allow Bowles to play in John Robertson's testimonial. Bowles was essentially understudy to the world's first £1 million signing Trevor Francis during his one season at the City Ground, and before the season was out Clough was already targeting Coventry City's top scorer Ian Wallace as his replacement. Bowles was then sold to Leyton Orient for £100,000 after making only 23 appearances in all competitions. He joined Brentford the following year and remained at the club until retiring at the end of the 1982–83 season. Bowles came out of retirement to briefly rejoin the club on a non-contract basis during 1983–84 season, before retiring again in February 1984. He received a testimonial in 1987, earning £17,000. Post-retirement, he continued to play at non-league level for Epping Town.