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City chairman Adam Pearson has previously ruled out a move for Windass as the club wouldn't be able to afford him, but things may be different now he's available for free.
He would still demand high wages, but has always stated his desire to return to Boothferry Park, and could see it as an ideal move now he's without a club.
The versatile player - who started out as a right-back and then became established as a central midfielder and forward - made just over 200 appearances for City in the early 1990s, scoring 64 goals.
His most recent to return to Boothferry Park came just weeks ago when he turned out for Boro in a pre-season friendly here.