Osborne-Paradis skied for the first time at the age of four. He competed in his first race when he was ten. From winter 1999/00 he regularly took part in FIS races and runs for the Nor-Am Cup in his home country , where he developed his skills in the fast downhill and super-G disciplines. He landed his first international success at the 2003 Junior World Championships in Serre Chevalier , France , where he was fifth in the downhill. After several top placements in the Nor-Am Cup, he finally moved up to the squad of the Canadian national ski team in 2004.
In January 2005 he made his debut in the downhill skiing of Chamonix in the Ski World Cup and went straight to the 14th place. In the following races, Osborne-Paradis confirmed his reputation as one of the greatest young hopes of the Canadian Ski Association. Occasionally he was placed in the top 20, including at the 2005 World Ski Championships in Bormio (19th place downhill, 17th place combined) and at the 2006 Winter Olympics in Turin (13th place downhill, 20th place Super-G). However, there were no top results.
That changed at the beginning of the 2006/07 season . At the first World Cup downhill, which was held in Lake Louise , Canada , Osborne-Paradis surprisingly finished second and at the end of the race was only five hundredths of a second behind the winner, Marco Büchel . At the 2007 World Championships in Åre he was ninth in the downhill, but at the 2009 World Championships in Val-d'Isère he was eliminated in both the downhill and Super-G. On March 6, 2009, Osborne-Paradis celebrated its first World Cup victory on the descent in Kvitfjell . Two more victories followed in November and December 2009. At the 2010 Winter Olympics in Vancouver , however, he only achieved 17th place in the downhill and did not finish in the Super-G.
On January 29, 2011, Osborne-Paradis crashed on the Chamonix descent after a driving error. He broke the head of the left tibia and several ribs. He had to take a break for the rest of the winter and could not take part in any races in the 2011/12 season.
On February 8, 2017, on his 33rd birthday, he surprisingly came third at the 2017 World Championships in St. Moritz . His start no. 26 proves that he was only in the third best group of elite runners. In November 2018 he suffered serious injuries during downhill training for his home race in Lake Louise , which meant that he had to take a break for the entire 2018/19 season .