Sidebottom played in Collingwood premierships 13 years apart, in 2010 and 2023, and won back-to-back Copeland Trophies in 2017 and 2018. The 184cm midfielder was All-Australian in 2018 and took the Gary Ayres Medal as best afield across that year's finals, and was a Magpies vice-captain from 2015 to 2022. He reached 350 games in 2025. He retired at the end of the 2026 season, having played 375 AFL games and kicked 213 goals.