Craig Brewster

Playing and managing Brewster left Dunfermline in November 2004 to become player/manager of Inverness. A run of poor results meant that Brewster left United in October 2006. He linked up again with Jimmy Calderwood, who had been his manager at Dunfermline. Brewster made his debut for Aberdeen as a substitute in a goalless draw with Hibernian on 2 January 2007, and he scored his first goal for Aberdeen with a header in a Scottish Cup tie against the same opponents eight days later. Brewster then suffered a dislocated shoulder in a draw against Inverness. Doubts were cast over his playing future, but Brewster returned in early March and he signed a six-month extension to his Aberdeen contract in May 2007.

His contract with Aberdeen was cut short, however, when he returned to management with Inverness in August 2007. He only played in two league games for Inverness in his second spell with that club, scoring the winning goal in a SPL match against Hearts. After being sacked as Inverness manager in early 2009, Brewster signed a contract with Highland derby rivals Ross County until the end of the 2008–09 season.

Coaching career

Inverness CT In November 2004, Brewster accepted the job of player–manager with Inverness Caledonian Thistle. He helped to establish the club in the Scottish Premier League after John Robertson had left to take the position at Hearts.

Dundee United

Brewster was appointed player–manager of Dundee United in January 2006. His return to United yielded little success, however, as despite going unbeaten in his first three games, the remainder of the 2005–06 season brought just one win (against Livingston). Brewster had to wait four league games into the 2006–07 season for his second league win, and oversaw only two league wins in his nine months at Tannadice.

On 29 October 2006, after a 5–1 defeat to Falkirk, Brewster and assistant Malky Thomson left by "mutual agreement". After leaving Dundee United he was linked with several managerial vacancies, including those at former clubs Dunfermline, Raith and Ionikos, but he returned to playing with Aberdeen instead.

Ross County

Brewster was appointed assistant manager of Ross County, working with manager Derek Adams. Ross County reached the 2010 Scottish Cup Final under their management. Brewster left the club in December 2010, soon after Willie McStay had replaced Adams as manager.

Crawley Town

After six months out of work, Brewster was appointed first team coach of Crawley Town by manager Steve Evans in June 2011. Brewster was appointed caretaker manager on 9 April 2012, after the departure of Evans, until the end of the season. Brewster guided the club to promotion to Football League One with three wins from their last six games. He was retained as a coach when Sean O'Driscoll was appointed manager in May 2012. Brewster was again placed in caretaker charge, along with Steve Coppell, after O'Driscoll left in July 2012.

After Crawley In November 2013, Brewster joined Whitehawk as assistant manager. He worked for Darren Freeman, but Freeman was sacked as manager in January 2014. Brewster subsequently moved to a coaching position with the youth academy at Brighton & Hove Albion.

Plymouth Argyle In June 2015, Derek Adams appointed Brewster to the position of assistant manager at Plymouth Argyle.

Brewster left Argyle at the end of the 2017-18 season, after a hip operation he had undergone in January 2018 had seen him not feature on the sidelines for Argyle for the back-end of the season. He was replaced as assistant by Paul Wotton, with Kevin Nancekivell stepping up to the first team coaching team. Brewster later expressed his sadness and surprise at being released by the club.

Horsham On 25 November 2019, Brewster was appointed sporting director of Horsham.

On 1 July 2021, Brewster was appointed Head of Youth Development at Horsham.