Freedman started his footballing career with high flying, QPR in 1992, however he didnt managed to make a first team appearance. He moved to Barnet on a free transfer in July 1994, aged 20. He made his league debut in August of the same year and quickly became the club's leading player, scoring 24 goals in his debut season.
The following season he signed for Cystal Palace for a fee of £800,000 in September 1995. He continued his goalscoring form managing to score a total of 20 times in the 1995-96 season.
The following season (1996-97) he only managed to score 11 goals but helped the club reach the promotion play-offs. He then scored very crucial goals, scoring in the 89th and 90th minutes of the semis after coming off the bench with 17 mins to spare. Palace went on to gain promotion to the Premier League.
Freedman's experience of football at this level only lasted 7 games, after which he was loaned initially to Wolverhampton Wanderers in October 1997, this was made permanent after scoring 2 goals in 2 games for the fee of £800,000, which was part of a combined deal for Palace defender Jamie Smith. Freedman's time at Wolves only lasted until the end of the 1997-98 season. He was the team's leading goalscorer with 13 goals, but the mergence of Robbie Keane convinced Wolves to sell him to Nottingam Forest.
He signed for the newly promoted Premier League Forest for a fee of £950,000 and made his first appearance on 17 August 1998 as a sub in a 2-1 defeat to Arsenal. In his first full season in the top flight he scored 9 goals for forest, who were then relegated to Div 1. He made a total of 83 appearances and scored 23 goals before being sold to Crystal Palace in October 2000.
Freedman signed back with his former club for £600,000, during a relegation threatened campaign, but one which ened with his most famous goal for the club. Relegation to the third tier loomed, until Freedman scored with 3 minutes to go, this kept Palace in the division, but relegated Huddersfield Town.
The following season he scored 21 goals in all competitions. This earned him a call up with Scotland, howver the follwing season he was dropped from the Scottish National team and started to only have limited appearances at Palace.
In 2003-04, under new manager Iain Dowie, he re-established himself into the first team and help guide the club to promotion. Back in the Premier League he was often overlooked as the team only used 1 striker. He scored his only top flight goal in their vital final fixture at Charlton Athletic, drawing them level at 1-1, however the match finished 2-2 and Palace were relegated again.
Back in the Championship he remained down the pecking order but appeared again for the club in November 2005 scoring his 100th and 101st goals for Crystal Palace. This made him the 7th player in Palace's history to have reached the century mark. He ended the season with 7 goals. The appointment of Peter Taylor as manager in Summer 2006 again limited Freedman's chances and he only managed to score 3 league goals.
Freedman joined Leeds United on loan and scored 5 goals which helped him to get rewarded with April's League One's player of the month and saw the side reach the Play off final, where he made an appearance on the day of his 34th birthday. At the end of the season he was no longer required by Leeds so returned to Palace. Freedman was granted a testimonial to reward him for his 10 years at the club.
Freedman again left Palace to join Southend on a free transfer, scoring 4 goals in his first 4 outings. Howver he was plagued by injury. In March 2010 his contract was terminated and this ended his playing career. He rejoined Palace as part of the coaching staff.
Freedman's coaching career started when he was appointed the reserve team manager of Crystal Palace in November 2007. He was in this role alongside his playing dutied for the club's first team. This role had ened on his loan move to Leeds. He also began coaching alongside playing for Southend United.
Freedman became the assistant manager of Crystal Palace, to Paul Hart, in March 2010, helping secure the survival of the Eagles. Following the appointment of Georgr Burley, Freedman was retained as the Assistan Manager. When Burley was sacked on New Year's day 2011 freedman was given the caretaker Manager role, check was only expected to be for a few weeks until a new manager was appointed, but he was made permanent manager, signing a 2 and a half year deal on 11 January 2011. He quickly moved to bring in Lennie Lawrence as his Assistant Manager.
He was sucessful in guiding the club out of the relegation zone with the club achieving safety with a game to go. Palace began the 2011-12 season well and were left in the play-off places at the end of October and had a good run in the Football League Cup, where they knocked out Man Utd 2-1 at Old trafford. Palace ended up finishing 17th place.
On 23rd October 2012, Palace announced Freedman has left to join Bolton Wanderers.