Benjamin was signed by the Worcester Warriors Academy. After suffering a fractured fibula at the Middlesex Sevens in August 2006, Benjamin returned to full fitness with the help of the Worcester Warriors physios after a year out, returning in the 2007 Middlesex Sevens tournament. Cousin, Marissa Dzotsi, who helped him through it all and was by his side and watched him play a great game. Miles plays centre and wing.
In November 2009, Benjamin agreed a two-year deal which will keep him at Worcester Warriors until 2012.[5] Despite suffering relegation during the 2009–10 Guinness Premiership, Benjamin stayed with the club.[6]
Leicester Tigers
Benjamin signed a deal with Leicester Tigers for the 2012/2013 season. In his first game for the tigers, in an 'A' League match at Northampton he suffered a serious neck injury which ruled him out for the rest of the 2012/2013 season. He finally made his 1st XV debut in October '13 against Ulster. His first scores for the tigers were in a Heineken Cup match against Montpellier where he scored a brace.[7] He scored his first Premiership try for Leicester on 5 January in a 27–27 draw against Bath. He announced his retirement on 24 March 2016 due to a longstanding injury.