The flanker played his 50th game for the team against a North Otago XV in Wanaka last month.
While at higher levels 50 games can be achieved in a few years nowadays, it is a far more impressive feat to in the Country team.The 35-year-old is in his 10th year in the team, having begun in 2005 and played every year except for when he was overseas in 2012-14.
He knew before the game it would be his 50th, but it was not until he was asked how many he had played that he was aware the milestone was coming up.
Despite that, it was something he said was good to achieve.
"Oh yeah, it takes a while to get there, it’s good," he said.
"I didn’t really know until I had a bit of an add-up.
"One of the players asked me and I just said about 50 and we had a bit of an add-up and it was 50, so it was good."
The 2009 season had been a highlight, the team travelling to Wellington to play Horowhenua-Kapiti, which it beat, and Wairarapa-Bush, which it narrowly lost to.
It then returned south and claimed the scalp of North Otago.
In that season Winter was named both Otago Country and Central Otago player of the year, while his Arrowtown club also won the Central Otago competition.
It was the second year in a row the Arrowtown team had won the Central Otago competition, although it was unable to claim the countrywide crown it took in 2008.
A stalwart of the club, Winter has played 169 matches for it since moving to the town in 2005.
Originally from Wyndham, he moved to Dunedin for his final year of school and boarded at Otago Boys’ High School.
He stayed on in the city, attending the Institute of Sport and playing for Zingari-Richmond.
After a year playing for Star in Invercargill, he was offered a building apprenticeship in Arrowtown and took the opportunity.
In those days he had been a second five-eighth, but chose to move into the forwards when he arrived in Arrowtown, preferring to be closer to the ball.
He has been there ever since, although took a two-and-a-half-year hiatus in Germany, starting in 2012.
That saw him play in the country’s top domestic league, while also working as a builder.
German rugby contained a lot of "monsters", although they were not very skilful, he said.
He returned to Arrowtown with his partner after deciding it was time to go home and also returned to the rugby club.
While admitting it is getting harder to bounce back from the knocks, he was not planning on slowing down.
"I’ll keep playing for Arrowtown for as long as I can, yeah, as long as the body lets me.
"It feels all right. It takes longer to recover now; it takes about a week now."
Otago Country had two games remaining this season, before the summer, during which Winter was hoping to build his house.