The two men, separated by just a year in age, first became familiar with each other as strikers in English football's top flight - indeed Freedman was playing for Nottingham Forest when Solskjaer famously reaffirmed his status as Manchester United's 'super sub' by scoring four times in 12 minutes in an 8-1 victory in 1999.
And the pair became better acquainted on coaching courses in the next decade when the Norwegian impressed Freedman with both his knowledge of the game and his passion, even then, to extend his career in football.
"I did my coaching course with him many years ago and this was the great thing I liked about Ole, he was still playing when he was doing these things," said Freedman.
"We were talking in football terms and still playing but looking to the future so it did strike me that one day he would be a manager or a coach, he's good at both."
Solskjaer, now 40, was dubbed the 'Baby-faced Assassin' at Old Trafford but, as he prepares for Saturday's clash at the Reebok Stadium, Freedman thinks that behind the youthful exterior the manager has a steely resolve to succeed.
"You get the feeling straight away when you meet him," the Scot said.
"You get a feeling he's serious, you get a feeling he's humble, you get a feeling he's educated himself in the football world.
"That doesn't mean he's going to be successful. Football's not fair, like life, it doesn't mean because he's done it he'll get results but he's given himself the best possible chance to succeed and that's very impressive in my eyes as a young coach.
"Being committed to your coaching badges, getting your qualifications, studying the game, looking at players - committed, that's what he is."
Wanderers loaned both Kevin McNaughton and Joe Mason from Cardiff earlier this season, and the two helped reverse Bolton's fortunes following a difficult start to the campaign.
McNaughton has found himself back in the first-team picture since the new year under Solskjaer.
However, Freedman, 39, has not yet been able to call on a favour from his old coaching-course buddy.
The Bolton boss said: "I spoke to him a couple of weeks ago and congratulated him on the job. I told him I'll see him in a couple of weeks and is there any chance of one or two of his players? He said, 'I'll see you next week, but no!'.
"It's a wonderful for job for him, I'm happy and he deserves it."
While Solskjaer is familiarising himself with proceedings in south Wales, his opposite number for this weekend is well aware of the task facing him at the Reebok Stadium over a year since his appointment.
Left with a wage bill which has contributed to the club's debt rising above the £160million mark, Freedman has been unable to transform a squad seemingly in need of an overhaul if promotion is to be achieved in the near future.
They looked far from promotion contenders when they were thrashed 7-1 by Reading last weekend, but the Trotters boss is hoping they can provide the perfect riposte in the cup.
"The minute the (final) whistle went at 10 to five, the preparation started for the Cardiff game," Freedman said.
"We have left no stone unturned on preparing the players and being honest with the players in terms of what we saw on Saturday."
Goalkeeper Andy Lonergan is unlikely to forget the afternoon at the Madejski Stadium in a hurry, and acknowledges the team must show a response in front of their own supporters this weekend.
Lonergan said: "That was the worst feeling I've ever had on a football pitch. I just felt as a team - we've all said it - we didn't perform.
"We lacked fight, which is something I really don't want to say. I was embarrassed on the pitch and I'm still embarrassed but we have to move on."