The carefree winger will play his 50th game for the Highlanders against the Stormers tonight and is thrilled to have brought up the mark.
"I think it is the first sort of milestone I have come across in rugby. I have never played 50 games for any team in rugby," he said.
"I got 41 for Canterbury. I was a bit upset I did not get there for Canterbury but injuries and that got me. So I am happy to have the 50 games."
Osborne made his debut for the Highlanders in the first game of 2014, a year when no-one fancied the side after a horror run in 2013.The side, though, made the playoffs and Osborne rode the wave again the next year as it went all the way to the title.
"I remember that first game and Malakai [Fekitoa] just cutting up. I think we were underdogs that game and then scoring my debut try for the Highlanders in that game.
"That was the first step in rebuilding the Highlanders from the year before. There were not too many well-known players. Malakai was not as famous as he is now. Everybody felt like they had something to prove, coming from other franchises and being the offcuts.
"We all just banded together and formed a brotherhood and it just went from there.
"Winning the Super rugby in 2015, it would be hard to beat that. Then beating the Crusaders every now and again ... there is a big rivalry there. One to look forward to."
Osborne said he loved playing with his fellow Fijian Waisake Naholo.
"We take it to another level when we are playing together. Hopefully we will bring it again against the Stormers."
Osborne (29) said he was thinking this would be the last season with the franchise.
"I’m just listening to the body and being smart. I’ll try and go to Japan and stay there for a bit longer. It is a bit easier on the body and you get four months’ break. That is always good for the body."
Osborne played last season in Japan for the Kubota Spears and would return there for the foreseeable future.
He declared for Fiji last year and playing in the World Cup in Japan in 2019 was a goal, but that was "up to the coach", Osborne said.
He made it into an All Black training camp early in the 2015 season but never got to play in a test.
However, he would make himself available for the Highlanders match against the British and Irish Lions on June 13.
He was not going to get too emotional about leaving the franchise and was just aiming to play every game as though it would be his last.
Arriving in Dunedin in late 2013, Osborne, who grew upin Suva, said he had expected the worst with his adopted town.
"I actually thought it would be the longest season of my life because every game I had come down to play in Dunedin, it was always raining and that. But the sunny days are wicked. Worth the wait.
"Then the city is so small you can get around easy. Just like Suva, really."