Despite further injury problems, he proved a vital cog in the wheel as Worcestershire won the 1988 and 1989 County Championships; it was during this period that he wrote, with team-mate Graeme Hick, an account of one of the title-winning seasons, entitled "Hick'n'Dilley Circus". Dilley's Test career was beginning to wind down by this time, and his final match was at Edgbaston in the 1989 Ashes series. He made certain that he would not be picked again by accompanying Mike Gatting on the rebel tour to South Africa that winter, although he continued to play for his county for a couple more years. Dilley appeared in three of Worcestershire's matches in April 1992, but despite a couple of appearances in the Second XI, he announced his retirement at the end of that season because of recurring injury problems. Dilley's move to Worcestershire denied him the financial security of a benefit season. He found employment after retirement as a coach, firstly for the England women's cricket team, and then accompanying the men's side on the tour to India in 2001/02. He also worked in a coaching capacity for Zimbabwe and Scotland. His last position was as head coach for Loughborough UCCE, where he was director of cricket for 11 years and coached, among others, Monty Panesar, James Anyon, Ruel Brathwaite, James Adams and Rob Taylor. Dilley was the father of the Worcester Warriors rugby union captain, Chris Pennell. Dilley died in a hospice in Leicester on 5 October 2011, aged 52, just one week after being diagnosed with oesophageal cancer. A memorial service was held in Worcester Cathedral on Wednesday 9 November 2011.