Maryhill Maitland was assistant to Ronnie MacDonald at
Maryhill Juniors. Together they won three consecutive
Evening Times Cup Winners' Cups. The trophy was retained from 1995 to 1998. The duo also won the
Central Junior League twice. They won back-to-back titles in 1997 and 1998.
Clyde With no professional playing experience and having been assistant to Ronnie MacDonald at
Junior club
Maryhill Juniors, Maitland became the manager of
Clyde in 1998, after his long-time mentor MacDonald took over as general manager. After a season working alongside MacDonald – who brought in a large contingent of players from the Juniors such as
Pat Keogh and
Scott McHarg – he guided Clyde to the
Scottish Second Division title in his first season in sole charge, winning promotion to the
Scottish First Division. He left Clyde in February 2002 along with MacDonald and other associates after a dispute over youth funding. Maitland's first game in charge of Alloa was not an easy game, a midweek
Scottish Cup third round replay away to
SPL opposition,
Livingston. Alloa fell behind to a
Paul Dalglish penalty before half time but rallied in the second half with great goals from
Robert Sloan and
Ross Hamilton to win 2–1. Maitland started to build his squad for the 2007–2008 season with the addition of nine new players including experienced defender
Derek Fleming and second time Alloa midfielder
Brown Ferguson. Maitland was sacked in May 2011 following the club's failure to avoid the relegation playoffs. to a role as the
Director of youth football overseeing their
youth system, during which time the club's
under-17 team qualified for the
UEFA Youth League in 2018. He became the chairman of Hamilton Academical in December 2018 when MacDonald stepped down from the role, and soon appointed
Allan McGonigal as
director of football and
Brian Rice as
head coach of the club, the latter replacing
Martin Canning who had held the more traditional manager role.
Return to Clyde Two decades after his departure as manager, Maitland returned to the club as Director of Football. In June 2024 he succeeded Gordon Thomson as chairman. == Honours ==