He began his career in umpiring after suffering injuries to his Achilles tendon, jaw and knee whilst playing for Rowville Cricket Club in Melbourne. Wanting to stay in the game, he began umpiring in the
Victorian Premier Cricket competition in 2009. 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. Gillespie umpired six matches during the
2015–16 Big Bash League season and a further four the
following season. He made his first-class debut on 15 February 2015 in the
Sheffield Shield in the
round 7 match between
New South Wales and Victoria at
Robertson Oval in
Wagga Wagga where
Doug Bollinger took a
hat-trick from his
end. He has since umpired a further nine matches with the latest the clash between
Tasmania and
Queensland at
Bellerive Oval in March 2017. Gillespie was accepted into the 2015 intake of the
Australian Sports Commission National Officiating Scholarship program where he will undertake professional development and identified training activities to be able to officiate the elite level. ==Personal life==