The Scot had a spell on loan at the club in 2008, but wanted to join Leeds United permanently.
This weekend sees arguably the two biggest teams in England, outside the Premier League, go head-to-head at Elland Road. A season record attendance is expected as Leeds United host Nottingham forest in the Championship.
The last First Division title winners face the two time European champions in a game between two of the league’s in-form outfits.
Of course, for the Nottingham Forest manager it is an important game for more than just his faint play-off hopes.
Leeds United fans will remember Dougie Freedman’s loan spell with the club with fondness. The Scot joined Leeds, who were then in League One, on loan in March 2008 from Crystal Palace and went on to have a big impact at the club.
He scored six goals and set up three in his 14 games with the club, as they reached the League One play-off final.
The following season Freedman was surplus to requirements at Palace and he admitted to the Yorkshire Evening Post in 2010 that he was very keen on a move to Leeds that summer:
"I was waiting for a call from Gary McAllister but communication seemed to break down completely. I'm not sure what happened.
"I read a few things in the paper saying I wanted a certain length of contract or I wouldn't move from London because of my family but that's a load of crap. I'd have taken a deal up there, no questions asked.
"Leeds are huge in stature but they're a close-knit club. It's a proud and loyal place and I bought into their mentality straight away. The intensity of playing at Elland Road – I've been without it ever since and not out of choice. It's something I regret."
The move of course never came off and he instead joined Southend United that summer. Now he has the chance to return to Elland Road once again, this time as an opposing manager. While he can expect a good reception from Leeds fans, that will not stop him trying to force a win against his former club.