He's been on the opposites side of a winning result at almost all levels of the game.
But there remains one that was so close yet slipped away; the chance to compete for a VFL premiership.
“The one I didn’t play in was probably the most important one, but that is life,” Preston said.
Moving from Geelong to Richmond ahead of the 1982 season, Preston went on to play a big part in helping Richmond book a spot in that year's grand final.
But a hamstring injury in the Tigers' second semi-final win over Carlton put Preston in doubt for the decider.
“I had got fit by mid season, and started playing well and played every game until the grand final, but tore my hamstring in that second semi-final against Carlton,” Preston said.
“We had two weeks to try and get it right, but it didn’t mend in time and I missed the grand final."
Grand final weeks are often filled with the best of stories, but also the tough luck tales.
This year it is players such as the Western Bulldogs’ Josh Bruce and Melbourne's Adam Tomlinson, who played big parts in their team's success before suffering season-ending ACL injuries.
“You feel terribly sorry for them, and you don’t know until you go out there if you'll win or lose, so it's something you never know,” Preston said.
“Any finals footy is a fantastic experience. When you run out on the ground and hear the roar, I think you grow a foot taller."
Growing up in Echuca, Preston went on to play football at Scotch College for four years, before returning to his home town to play for the Murray Bombers in 1976.
The team would go on to play in a losing grand final against Seymour, before Preston was scouted by Geelong for a move to the VFL.
Remembering his transition "from the country to a bigger city", Preston said it was "intense but all worth it in the end".
Playing 58 games across five seasons at Geelong, Preston would finished his time at the club with back-to-back reserve premierships in 1980 and 1981.
With the under 19s, reserves and seniors all playing on the same day, Preston said the experience was like no other.
“It was enormous; by the time the reserves were finishing, the seniors would be about to start, so the place was packed,” he said.
“The roar of the MCG, it’s something you never forget.
“We had a reunion a couple years ago, and it was great to catch up with all the fellas I hadn't seen in 40 years; when you win a premiership together, there is always a special bond.”
A move to Punt Road ahead of the 1982 season came about after Preston realised he wasn't getting the right senior opportunities under Geelong coach Bill Goggin.
And a year after missing that 1982 grand final with the Tigers, Preston finished up at the club on 76 career games and returned home to play at Echuca.
Two years later, it was a phone call from former Richmond teammate Mick Malthouse that coaxed Preston back to the big time, this time at Footscray.
“He was coaching there at the time, and rang me up and said did I want to have another crack at football?” Preston said. "And I said, ‘yeah okay'. So I packed my bag and headed back."
Further hamstring injuries meant Preston only managed two games with the Dogs, before deciding he had had enough, and returned to Mathoura and the farm.
He would go on to play football with Bunnaloo, coaching the club to back-to-back premierships prior to the Echuca league folding.
Ahead of Saturday’s decider, Preston said he would have a soft spot for the Bulldogs from his time at the club, although a breakthrough Melbourne flag would be "a big win for football".
But most of all he is just hoping for a close game after the preliminary finals both blew out.
And from one Echuca player to another, Preston is excited to watch Clayton Oliver run out in the decider.
“I’d just like to wish Clayton well in the grand final,” he said.