Olli took his first World Cup win in Oberstdorf on 14 February 2009 with both jumps over 200 metres, including a hill record of 225.5 m which has stood for 8 years.

Upon questioning by British Eurosport commentator David Goldstrom, the Finnish coach Janne Väätäinen stated that Olli's apparent disinterest stemmed more from "frustration" and shyness than a bad attitude to ski jumping.

[5] In the team event, Olli acted as anchorman in place of Ahonen, improving under the weight of responsibility and making two very good and consistent efforts.

However, due to a sudden flurry of good form for the Norwegian team, Finland placed just outside the medals in a closely fought final round.

[7] On 28 November 2010 Olli was suspended by the FIS for one competition after 'flipping the bird' to the media camera after his poor qualification jump of 77 m which left him in 57th place.