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His FIS Ski Jumping World Cup debut took place on 29 December 2009 at the Four Hills Tournament in Oberstdorf, having previously gained success in the Continental Cup. On 3 January 2010, he succeeded in Innsbruck with a 30th place-his first World Cup point. At the FIS Ski-Flying World Championships 2010 in Planica he reached the 28th place in the individual event.
In his second season, he won the third place with the German team in Oberstdorf in 2011.
At the beginning of the 2011/2012 World Cup, he finished 9th in Kuusamo. In Lillehammer on 3 December 2011 he reached the second rank, his first podium placing. A week later he won the competition on the large hill in Harrachov ahead of Thomas Morgenstern and his teammate Severin Freund. At the same jump, his father Holger Freitag celebrated his only World Cup victory on 8 January 1983. On 20 January he clinched 2nd spot in Polish Zakopane, behind home favorite Kamil Stoch, securing his 3rd individual podium of his career.