Bolton previously was the head coach of the Carlton Football Club in the AFL, having served in the role from 2016 to 2019.

[6] Bolton served as the head coach of Victorian Football League club the Tasmanian Devils in 2006, taking over from former Fitzroy and North Melbourne player Matthew Armstrong, who left the club due to internal pressure from the Devils' playing group.

He served as head coach for the remainder of the season, after which he was replaced with former Sydney Swans player Daryn Cresswell.

The Hawks defeated Geelong in the First Elimination Final, before narrowly losing an epic semi-final to Port Melbourne 19.10 (124) to 19.14 (128).

In Bolton's second season in charge of the club, the Hawks built on their improved form in 2009 with another strong performance in 2010.

The Hawks met the Bendigo Bombers at the Box Hill City Oval in the First Elimination Final, prevailing by 65 points, 20.16 (136) to 10.11 (71).

In circumstances similar to that of the previous season, Box Hill won its Elimination Final in strong fashion and again met Port Melbourne in the First Semi-final.

The following week, the Hawks met North Ballarat in the Preliminary Final at the Box Hill City Oval.

[19][20][21][22] Before his sacking, the club under Bolton had won only one of its 11 matches in the 2019 season, sitting at eighteenth, which is the last position on the ladder.

At the end of the 2021 season, Alastair Clarkson was replaced as senior coach of Hawthorn by Sam Mitchell.