Despite being injured for most of the 2008–09 season, MacGregor was given a contract extension by Davie Irons until August 2009 to prove his fitness ahead of the next season. After receiving the extension, which was until 15 August 2009, MacGregor managed to regain the ability to run in June 2009 ahead of the season to give him hope of gaining a contract extension for the rest of the season. On 17 August, MacGregor signed a new one-year deal to take him until the end of 2009–10 season.