 In June 2007 O'Brien rejoined Dorchester  and following Shaun Brooks' resignation, he was appointed player-manager on 5 March 2009.On 22 November 2009, after just eight months in charge of Dorchester Town, Roy was relieved from his duties as a manager, due to the clubs poor showing in cup competitions.On 28 June 2010, he was appointed manager of Yeovil Town Ladies and will manage them in their first ever season in the FA Women's Premier League, before becoming the club's first team coach and subsequently working with the Yeovil Town Community Sports Trust.