When Paul Scholes took over as first team manager at Boundary Park, Sheridan predicted the Manchester United and England legend would quickly find out just how hard football management can be.
Thirty one days after taking charge of the League Two club, with one win in seven games, Scholes quit, saying: "It unfortunately became clear that I would not be able to operate as I intended and was led to believe prior to taking on the role."
Chesterfield boss Sheridan, father of Oldham defender Jay, said he always thought it was a 'funny' appointment.
"I just felt when he went in there it was a funny one," said Sheridan senior.
"I know Paul, I know he supports Oldham and I know every time someone loses their job there's talk of him getting involved.
"My lad is there, he's a young pro there and he really liked Scholes. Scholesy was really good with him, spoke to him, looked after him."
While Sheridan concedes any new manager has got to start somewhere, he pointed to 'unsettled' circumstances behind the scenes at Oldham which make it a difficult job.
"You've got to learn somewhere," said Sheridan.
"He's gone in there, the club is very unsettled at the moment.
"I always found it a bit of a funny one, I don't think he needs Oldham, Paul Scholes.
"Whatever is behind the scenes has unsettled him, or whatever has gone on, I can't really comment on it too much.
"He's made his decision now and they'll move on won't they?"
Sheridan played 144 league games as a Latics player, over six seasons.
He took over as caretaker manager in 2001 and again in 2003, before becoming permanent boss in 2006.
In 2009 he departed by mutual consent, but he was back in charge in January 2016 and guided them to League One safety.
Oldham reappointed him in January 2017 and once again saved them from the drop, before leaving by mutual consent in the September of that year.
The current Latics squad includes three former Spireites, in Giles Coke, Chris O'Grady and Dan Gardner, whose season was ended by a serious knee injury.