Sidebottom started playing as a young boy for Kirkburton Cricket Club. He made his debut for his native Yorkshire in 1997. The winner of the NBC Denis Compton Award two years running, (in 1999 and 2000), he finished as the leading domestic English-bowler at the end of 2000, conceding only 12.5 runs for each of his 24 wickets, and capping this with a nomination for Cricketer of the Year by the Cricket Writers' Club. Injury problems took away much of his 2000 season, but, during the winter, Sidebottom toured the West Indies with England A, taking 16 wickets at a bowling average of 16.81. He made his international debut the following summer against Pakistan in place of Matthew Hoggard. He played in two ODIs in October 2001 against Zimbabwe.

Sidebottom left Yorkshire to join Nottinghamshire at the end of the 2003 season, having taken 163 wickets for Yorkshire at an average of 25.12. At Nottinghamshire, he took 50 wickets in both the 2005 and 2006 seasons, helping them to the County Championship title in 2005. He has won five County Championships in total; he won the title with Yorkshire in 2001, 2014 and 2015 after returning to the county of his birth, and with Nottinghamshire in 2005 and 2010.

He sports a flamboyant hairstyle which has led to the dressing room nickname of "Sexual Chocolate". Sidebottom's long hair indirectly led to a second nickname, "Stringfellow", after a hapless Henry Blofeld repeatedly confused him with long-haired nightclub impresario Peter Stringfellow during the first Test match against New Zealand in 2008.

On the 22nd February 2017, Sidebottom announced that he would be retiring from first-class cricket in all formats, commencing at the end of the 2017 County Championship. He now runs a Cricket Academy and Foundation.

Sidebottom was appointed bowling consultant for Surrey, on 14 March 2018.