Assumption University

At Assumption, Sidebottom left his mark as a player, coach, and captain. He earned a plethora of achievements throughout his collegiate playing career. Sidebottom was named to the Northeast-10 All-Conference Second Team in 2008 before being named to the Northeast-10 All-Conference First Team and Worcester Area First Team All-Star following his junior campaign. He also achieved in the classroom, being named to the Assumption Student-Athlete Honor Roll in 2009 and 2010. He followed up his 2009 athletic achievements by being named to the Northeast-10 First Team All-Conference selection, as well as the 2010 Northeast-10 Offensive Lineman of the Year before being named to the Super Region One Second Team. For his career, he appeared in 28 games (19 starts), with three rushes for 11 yards, one touchdown, and four tackles, which is unique for an offensive lineman.
 
Upon graduating, Sidebottom helped coach the Greyhounds for three years. He worked with the running backs and tight ends in 2011 and 2012 before moving to the offensive line in 2013 while also serving as the Hounds' strength and conditioning coordinator until 2014.