[1] Oldershaw did qualify for the 2008 Summer Olympics, there at Beijing he suffered further disappointment, missing the final of the C-1 500 m event.

At the 2011 World Championships in Szeged, Hungary Oldershaw came 5th in the C-1 1,000 m. He then qualified as part of Canada's team for the 2012 Summer Olympics,[2] he won a bronze medal in the C-1 1,000 m event.

The whole race I was just staring at the nose of my boat, there’s a big maple leaf on it, and it’s just such a good feeling.

"[1] On July 1, 2015 Oldershaw was named the flagbearer of Canada at the 2015 Pan American Games opening ceremony.

[6][7] Oldershaw is also close friends with Olympic teammate Adam van Koeverden and trains together with him at the Burloak Canoe Club.