Despite only spending a short spell at Barnet at the beginning of his playing career, Freedman was voted as the fans' favourite player in the club's all-time history in late 2007.
[7] Freedman's experience of Premier League football in the 1997–98 season proved short-lived though as he only managed seven top flight games before being sold to Wolves.
[7] After impressing with two goals in as many games, Wolves quickly made his contract permanent in a £800,000 combined deal with Palace defender Kevin Muscat.
However, the next season was less of a personal success as he was dropped from the Scotland side, and began to find his appearances limited at Palace, as manager Trevor Francis largely preferred Ade Akinbiyi, Dele Adebola, and Andy Johnson to him.
However, life in the Premier League in 2004–05 saw Freedman often overlooked as the team employed only one striker in most games, with Johnson being the preferred choice in this role.
Despite attracting interest from Leeds United midway through the season, he remained committed to the Palace cause of consolidating Premier League status by rejecting a loan bid from the Championship contenders.
He stayed to score his only top flight goal for the club in their vital final fixture at Charlton Athletic, drawing them level at 1–1.
However, injuries to Johnson and Jon Macken, and lack of form from Morrison brought him back into the team and he scored his 100th and 101st goals for Crystal Palace in a 3–2 win at rivals Brighton & Hove Albion on 20 November 2005.
Taylor was replaced by Neil Warnock early in the 2007–08 season, but strong goalscoring form of Clinton Morrison limited Freedman to rare substitute appearances.
[19][20] This form earned him League One's "Player of the Month" award for April,[21] while another vital late play-off goal in the first leg of Leeds' semi-final tie with Carlisle United and an assist for a last minute Jonny Howson goal in the second leg helped the Whites to Wembley, where he featured in the play-off final on the day of his 34th birthday, as Leeds were downed 1–0 by Doncaster Rovers.
In March 2010, Freedman had his contract at Southend terminated by mutual consent to rejoin Palace as part of the coaching staff, signalling the end of his playing career.
[24] Scotland manager Craig Brown considered selecting Freedman for the full national side in 1996, when main striker Kevin Gallacher was injured.
After his retirement from his playing duties, in March 2010, Freedman returned to Crystal Palace, now as the assistant manager to Paul Hart, with John Pemberton as first team coach.
[31] At this time, Palace were in administration, with the new coaching staff's task being to avoid relegation from the Championship, which was achieved on the final day of the season.
Palace began the 2011–12 season well under their new manager, occupying the playoff places at the end of October and also enjoying a good run in the Football League Cup, where they knocked out Manchester United 2–1 at Old Trafford with goals from Darren Ambrose and Glenn Murray.
On 23 October 2012, Crystal Palace released a statement announcing "that first team manager Dougie Freedman has joined Bolton Wanderers.
He continued to lead Bolton Wanderers to five consecutive wins (last done in 2006) in the late push for promotion, taking the club from 20th to 7th position in the Championship.
After guiding Bolton to a late push for the play-offs,[42] Freedman won the Football League Championship Manager of the Month award for April 2013.
Following a 3–0 defeat to Sheffield Wednesday at the City Ground on 12 March 2016, in which eight Forest players were unable to play because of injury, Freedman was sacked the following day.
[50] In the summer of 2021, Freedman played a big role in helping bring former Arsenal captain Patrick Vieira to Crystal Palace as their manager.
He also secured the loan signing of Conor Gallagher from Chelsea as well as permanent deals for centre-back Marc Guehi and winger Michael Olise.
All three signings turned out to be pivotal in the ensuing campaign as Crystal Palace reached the FA Cup semi-finals for just the fifth time in their history.