Eagles was initially linked with two of the Championship promotion favourites Cardiff and Derby during the pre-season but the closest he came to a new contract was at Bradford City.
The recent shenanigans at Blackpool might have opened a door for a return. Had Owen Coyle, last week's Fantasy Football motor mouth, landed the Bloomfield Road job he was expected to sign Eagles for a third time.
Nothing came of that but he's now having a trial with Millwall and it's in the boxing ring where he has been preparing for it.
Speaking to Marc Iles of the Bolton News just over a week ago, Eagles said: "I went down to a boxing gym in Moss Side and I can't thank them enough for what they have done. I feel really great at the moment, it has been a supportive environment, and I'm ready to go again now.
"I've had a few options; it could be two days, it could be two weeks, but I've been up at 6:30 a.m. every morning working with some really great people who have really helped me a lot."
Could he find a career in boxing? "I don't think so. I'm not cut out for that," he said.
Millwall has been a ground where things have not gone quite right for him in the last couple of years. In 2012/13 he missed a penalty there. It would have given Bolton the win but it all turned sour when Darius Henderson won it for the home side in stoppage time.
That proved the last straw for the hierarchy at Bolton and Coyle lost his job immediately after this game.
In the same fixture last season, on 15th February, Eagles lined up for the last time in a Bolton shirt. In a 1-1 draw, with Lukas Jutkiewicz scoring the Bolton goal, he was replaced on 73 minutes by Neil Danns and wasn't selected again for Wanderers.
He'll now be hoping for some better fortune at the Den as he looks to impress manager Ian Holloway and win himself a way back into the game and a contract with Millwall.