Sidebottom was selected by Collingwood with selection 11 in the 2008 AFL Draft. Sidebottom had a 10-goal best-on-ground performance in the 2008 TAC Cup Grand Final. He is strong overhead and in one-on-one contests. An AIS/AFL Academy graduate and Vic Country representative in 2008, Sidebottom also was selected in the All-Australian team following the 2008 AFL National Under 18 Championships.
In 2010 Sidebottom played in all but one game for the Magpies including both the drawn Grand Final and Grand Final replay. At 19-years of age he was the youngest member of Collingwood's 2010 Premiership side.
His older brother Ryan plays cricket for the Victorian Bushrangers