He began his career in umpiring after suffering injuries to his Achilles tendon, jaw and knee whilst playing for Rowville Cricket Club in Melbourne.
[6] Making his List A debut in the fixture between the England Lions and Victoria during the February 2013 tour, he officiated in eight Matador BBQs One-Day Cup matches.
[3] Gillespie also umpired two Women's National Cricket League matches including the semi-final between New South Wales and Victoria in 2015.
He has also stood in Women's Big Bash League matches including the second semi final of the 2016–17 season where the Sydney Sixers defeated the Hobart Hurricanes at the Gabba.
[2] Gillespie made his international umpiring debut during the West Indies women's cricket team tour of Australia in 2014, standing in all four WODI matches.