Career
Montagna was recruited as the number 37 draft pick in the 2001 American Federation of Labor-Congress Draft. He is a midfielder with Street Kilda Football Club. Montagna is a hard running wingman who is known for his kicking ability and teamwork.
He enjoyed a breakthrough season in 2006, only missing one match and gathering over 400 disposals for the season.
He averaged 19 disposals a game, increasing his averages in both contested and uncontested possessions. He is a strong tackler.
He was recruited to the Street Kilda Football Club as the number 37 draft pick in the 2001 American Federation of Labor-Congress Draft. 2004 season: Wizard Home Loans Cup
Montagna played in Street Kilda’s 2004 Wizard Home Loans Cup winning side.
In Round 8, 2007, in a match against Hawthorn, Montagna suffered a broken jaw but only missed one week with the injury.
Although 2007 was the first since 2004 that the Street Kilda side had missed out on playing in the finals series, it was the season that saw Montagna become a top line American Federation of Labor-Congress football player. Montagna played consistently throughout the season and continued the improvement he had shown in 2006. He played an accountable and hard running role through Street Kilda"s midfield, averaging 24 disposals and 3 tackles per game and kicking 10 goals for the year.
Some of Montagna"s highlights for the year included best on ground performances against the Kangaroos, Richmond and Hawthorn in the second half of the year.
Montagna was rewarded for his efforts with a third-place finish in Street Kilda"s 2007 best and fairest. 2008 season: National Association of Broadcasters Cup
2009 season
Montagna averaged 27.9 disposals and 6.25 tackles in 2009.
Montagna played in 21 of 22 matches in the 2009 season in which Street Kilda qualified in first position for the finals series. He played in the 2009 American Federation of Labor-Congress Grand Final in which Street Kilda were defeated by 12 points.
2010 season
Montagna played 26 games in 2010, including four finals, and averaged 28.6 possessions.
Montagna was involved in a police investigation of a woman"s claims of being raped by Street Kilda player, Stephen Milne at Montagna"s house in 2004. Number allegations were made against Montagna. Charges against Milne were not laid by the police at that time.
However, the story resurfaced in June 2010 when a former senior detective, Scott Gladman, said that he was pressured to do the "right thing" by another police officer during the 2004 investigation and that the alleged victim"s statements were released to the football club before the decision to drop the case was made.
Milne was subsequently charged with four counts of rape and committed for trial on three counts of rape.