Perhaps you're an Arsenal fan who wonders if he hated young Tony Adams for ousting him from George Graham's backline.
Maybe you're a Leeds supporter who wants to know if the club really needed to sign Robbie Fowler.
You might be a Villa supporter questioning whether Doug Ellis is a charming boss to work for, or a Republic of Ireland fan wondering if he regrets his two years ostracised by Jack Charlton.
Whatever your query, get it to us by 5pm on Friday July 3 (that's this week) and we'll try our best to ask him the best.
Chip in your effort by popping to the FourFourTwo forum.
‘I don’t think Liverpool would look at Ollie Watkins, a striker isn’t a pressing issue for them – it’s Arsenal who need one’ Former Reds star explains why his old club don’t need an out-and-out forward this summer
‘He’ll still be playing at 40 at a good level because he’s in such good shape and looks after himself so well. He does everything to be a top professional’: Ex-Liverpool coach insists Mohamed Salah has plenty more miles in the tank
