Gleeson is still running around for the Tigers this season as a 41-year-old after more than 350-matches in the yellow and black.

After playing in the 2019 senior flag as a 39-year-old, the veteran Tiger is still getting a kick in the reserves this season and played one senior match against Holbrook.

Parr will notch his 200-match milestone with Osborne on the weekend when it hosts Billabong Crows.

The 36-year-old is closing in on 300 matches after playing close to 100 matches with home club Coolamon before joining Osborne in 2009.

"Since I'm getting into the twilight of my career, getting to 200 matches at Osborne is something that I do cherish," Parr said.

"I first arrived at Osborne in 2009 for a bit of a change and never did I think for a moment that I would be still at the club 13 seasons later.

"To be still playing for a proud club like Osborne - it's hard to put into words - but it does mean a lot to me.

"I always had intentions of going back to Coolamon to play alongside some good mates who I grew up with.

"But to be honest, it would be too hard to leave Osborne now.

"Hayden Gleeson played in the club's most recent flag when he was almost 40 and if my body can hold up I intend to try and match the old fella."

Parr originally followed boom full forward Brendan McKelvie from Coolamon to Osborne in 2009.

He played in a flag in his first season with the Tigers under coach Graham Hart.

The triple premiership player also achieved the ultimate success under Daniel McAlister in 2012 and Matt Rava in 2017.

Parr missed the Tigers' 2019 flag triumph with a torn ACL.

"I feel fortunate to have played under some outstanding coaches and I've had some crackers," Parr said.

"Matt Hard back in my Coolamon days is a bloke that I have a lot of respect for.

"Graham Hart was an outstanding coach and I'm one of the few blokes that calls him 'Grizzle' because he could get cranky at times.

"My personal favourite would be Daniel McAlister who would have had the biggest influence on my career.

"Macca helped me a lot both on and off the field.

"Matty Rava is also a terrific coach and I played against him when I was at Coolamon when he was at Ganmain and is someone that I have got a lot of admiration for."

Parr is also a huge fan of coach Joel Mackie who has the Tigers sitting on top of the ladder and undefeated after 12 rounds.

"Joel is big on structure," he said.

"With or without the footy we stick to our structures and everybody is a leader.

"Whether you have played less than 10 matches or more than 200, everybody is a leader.

"Joel has pinned a lot of faith in the kids and believes in what they can achieve this season."

Parr grabbed a slice of history in 2017 when he won the Azzi medal, played in his third flag and won the Des Kennedy for best-on-ground in the decider.

He revealed an injury riddled 2016 was the motivation for him to produce the most outstanding season of his glittering career.

"It was probably the first time that I trained consistently over the pre-season," he said.

"I tore my PCL during 2016 and only got back for the last month of the season plus finals.

"I probably struggled a bit to regain form so I started taking the pre-season a lot more seriously and have ever since."

Undoubtedly the secret to Osborne's sustained success is the seemingly endless supply of talented juniors that emerge through the club's junior ranks.

Parr co-coached the Tigers' thirds in 2019 alongside Connor Galvin and again last year in the Riverina league.

He also had a stint at the helm as coach of the thirds interleague side.

Parr said the tight bond between the players was a major part of their success.

And while Parr has enjoyed many highs over his career, the lowlight was a season ending knee injury suffered early in 2019 which ultimately cost him a fourth flag.

"I think when I did my knee and being the age I was most people thought I was done and dusted," he said.

"But personally I thought I still had a lot to offer.

"I stayed involved with the club by coaching the thirds and being amongst it, you soon get itchy feet again to be out there playing.

"A lot of blokes run around in the seniors in the bush until their late 30s and there is probably no better example of that than big 'H' (Gleeson)."

After more than 12 months on the sidelines, Parr has made a successful return to the Tigers this season.

The athletic tall has reinvented himself under Mackie and has played across half-forward as well as spending plenty of time on a wing.

"Joel surprised me a bit when he wanted me out on a wing," he said.

"It's certainly a different role but you have a fair bit of freedom and you are in the play a lot more."

Having the luxury of playing Parr on a wing underlines how strong a list Mackie has at his disposal this season.

In a scary proposition for the Tigers' rivals, Parr felt this could be the strongest line-up he has been a part of.

"I feel with the structures that Joel has implemented, that we are ultra consistent week in, week out," Parr said.

"The young kids are coming through which has been a hallmark of all the flags that I have been a part of.

"Joel has instilled that belief in the kids and it's those players that are under-25 that have been instrumental to our success so far.

"It's a big statement but in my opinion this is the best side that I have been a part of."

Parr rated Brock-Burrum duo Dean Murphy and Trent Storey alongside dual Azzi medallist Peter Hancock among his most toughest opponents.

Tigers president Jason Gooden remembers when Parr first arrived at Tigerland.

"I will admit Jamie didn't look like a footballer and looked a bit on the skinny side," Gooden said.

"But it didn't take long for him to prove me wrong.

"His athleticism and leap made him hard to combat whether in the ruck or up forward.

"His raking right foot was also damaging, especially on the run where he land long range bombs from outside 50m on a regular basis.

"Jamie has been a leader both on and off the field and we wish him all the best for his milestone match."