Ex-Congupna, Murray Under-18s, Scotch College and Oakleigh Under-18s. He was drafted on the back of a stunning 10 goal effort in the TAC Cup Grand Final. While he did not have great pace Sidebottom's skills on either side of his body and his great composure made him a player who instantly looked at home at the top level. He had 11 senior games in his first year and performed well in the finals. In 2010 he continued to improve and was a star in the Replay when his work in the forward half earned him a high standing in the Norm Smith Medal voting and was instrumental in the premiership win. He went from strength to strength in the succeeding years and built his endurance so he could spend more time in midfield. His judgment and delivery of the ball made him a key player in the Collingwood line-up. In 2013 he ran third in the best and fairest.