Before coming to Kyabram, the batsman endured a struggle to have his visa application processed.
ow he has been faced with the fight of his life, trying to get out of Australia and get home to his family in Ireland.
With the airline industry almost coming to a standstill due to coronavirus, the 23-year-old has been forced to extend his stay in northern Victoria.
But there is now light at the end of the tunnel for Gillespie, who is scheduled to fly out on Thursday.
“I’ve had to take everything one day at a time because everything has changed so quickly,” Gillespie said.
“I was meant to leave on March 30, but that quickly changed when Emirates said they were cancelling all flights after March 25.
“On the 23rd, I drove to the airport to see if I could get on a flight and I was told the flight leaving that night was full and would be the last one for the foreseeable future.
“Not knowing what was happening certainly threw me around a bit, but I’d just had to take things as they came.
“When that happened, I came back to Kyabram and have been trying to work out what I was going to do.
“I was fortunate Qatar Airways announced some more flights to Ireland which will allow me to get home.”
After returning home to County Tyrone in Ireland’s north, he will enter two weeks of isolation as per government requirements.
And it will be the perfect opportunity for Gillespie to spend time with his family after playing non-stop for the past two years.
“It’s going to be nice to be able to have an extended break,” he said.
“I haven’t seen my family since November when I came to Australia and cricket can keep you away from them for an extended period.
“In the last 24 months, I haven’t really had a rest, so it will be good for me, mentally and physically.”
Just when Gillespie plays his next competitive match remains to be seen, after Cricket Ireland announced its season had been postponed until at least May 28.
Back home, the former Ireland A representative plays for the North-West Warriors and has represented the side in all three formats of the game.
And Gillespie believes playing in the local competition gives him a great opportunity to continue developing his skills.
“There is a possibility that this season might not go ahead, but it is understandable considering what is happening in the world,” he said.
“The competition has Irish internationals, so being able to play against those guys is always a great learning curve.”
Cricket has always played a major part in Gillespie’s life, with his uncle Peter having played for the national team more than 100 times between 1995 and 2007.
“He is someone I have always looked up to,” Gillespie said.
“He had a fantastic career for the national team and one day I would love to follow in his footsteps.
“Since I started playing when I was eight, I have wanted to play for my country.”
During his first season with Kyabram, Gillespie averaged 30.4 with the bat in his eight Haisman Shield matches.
And he said he was hoping to return later in the year.
“I would love to come back and play for Kyabram again,” he said.
“I didn’t know what to expect when I first arrived, but I’ve loved every minute of my experience.
“The club and myself have started talking about me coming back, but it would depend on the situation with the coronavirus.”