At age 19, Bolton played in the 1998 TFL Grand Final. He won the Darrel Baldock Medal for the best player on the ground that day. Bolton would then play 24 games for the Tasmanian Devils in the 2001 and 2002 Victorian Football League seasons. At twenty-four, Bolton was appointed Captain-coach of North Hobart and he led them to the 2003 premiership. He won the Horrie Gorringe Medal that season. His playing career was cut short by a hamstring injury in 2008.
Coaching career
Brendon Bolton served as the head coach of Southern Football League club North Hobart, guiding the club to a Southern Football League Premiership in 2003. Bolton served as the head coach of Victorian FootballLeague 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. In 2008, Bolton served as the head coach of the Clarence Football Club in the Tasmanian Football League. Bolton was appointed the head coach of the Box Hill Hawks on 6 November 2008. In his first season with the club in 2009, Bolton enjoyed a relatively successful season in charge, the Hawks finishing 5th on the VFL ladder, with 12 wins and 6 losses. The Hawks defeated Geelong in the First Elimination Final, before narrowly losing an epic semi-final to Port Melbourne 19.10 to 19.14. 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. After an indifferent start to the season, the team came home strongly with seven consecutive wins in the second half of the season to again finish 5th on the ladder, with 11 wins and 7 losses. The Hawks met the Bendigo Bombers at the Box Hill City Oval in the First Elimination Final, prevailing by 65 points, 20.16 to 10.11. 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. In tense a match played in quagmire conditions at North Port Oval, the Hawks defeated Port Melbourne for the first time in a finals game 14.11 to 12.17, with the winning goal coming in the dying seconds. The following week, the Hawks met North Ballarat in the Preliminary Final at the Box Hill City Oval. Despite enjoying home ground advantage, the Hawks went down to the Roosters 16.18 to 6.17 who went on to claim the VFL premiership the following weekend. In his two seasons in charge of the Box Hill Hawks, Bolton coached 41 VFL Games including finals, achieving 26 wins and 15 losses for a winning percentage of 63.41%. As a result of his good performances as the head coach of Box Hill, Bolton was promoted to an assistant coaching role with the club's AFL affiliate Hawthorn.
Hawthorn
In 2014, Bolton coached the Hawthorn Hawks in a NAB Challenge Cup match against North Melbourne, with Hawthorn achieving a 65-point win. He was the interim coach of the Hawthorn Football Club after head coach Alastair Clarkson was hospitalised and diagnosed with Guillain–Barré syndrome in May 2014. After five matches, Clarkson received an endorsement from his doctors to resume his role as head coach. Bolton is the only man in the club's history to coach the club to five successive victories in his first five games.
Carlton
On 25 August 2015, Bolton was announced as the head coach of the Carlton Football Club for the 2016 season, succeeding interim coach John Barker who had been filling in for the sacked Mick Malthouse. Brendon Bolton's first win at Carlton came on the back of a hard fought 4 point win over Fremantle at Domain Stadium. On 3 June 2019, Bolton was sacked as senior coach of the Carlton Football Club after being defeated by the Essendon Football club in Round 11, 2019. Before his sacking, the club had won only one of its 11 matches in the 2019 season. Following the conclusion of the 2019 season, Bolton returned to Hawthorn to serve as the club's director of coaching.
