Jamie died from a heart attack on 31 August 2008, whilst out jogging near his home in Bathgate, West Lothian. A post mortem revealed he suffered from cardiac ischaemia, a hereditary condition from which his father had also died, aged 44. Jamie had been due to play for a Motherwell Select team on 11 September 2008, in a testimonial match for former team-mate Dougie Arnott. His sudden death came just eight months after that of his former Motherwell team mate Phil O'Donnell, who died from a similar condition shortly after collapsing during a Scottish Premier League game for Motherwell. Just 11 months later, another of Dolan's former team mates – Paul McGrillen – died by suicide, bringing the number of players from Motherwell's 1991 Scottish Cup winning side to have died to four, starting with the sudden death of Davie Cooper in March 1995.