The former Leeds United hero has admitted he is saddened by the club.
Cherry, who played over 400 times for Leeds, said: “I think the whole current situation at Leeds is very sad. The fanbase is fantastic and it’s a one-club city. But the club seem to just goes around in circles. They have got to start winning games, simple as that.”
Cherry's frustration is no doubt shared by many among the Leeds fanbase, with every season starting with promise and ending with despair.
It is the same story every year, and this lack of progression at Elland Road has made hopes of winning promotion to the Premier League an outside shot.
There is no easy fix for Leeds’ travails, although the recent team seems to be improving under the ownership of Massimo Cellino.
He has hired a head coach with a forward thinking mentality and good reputation in the Football League, whilst also signing a number of players who are better than Leeds have had for a number of years - the likes of Chris Wood, Sol Bamba and Stuart Dallas come to mind.
However, despite all these changes, the situation has yet to improve, and Leeds sit 16th in the Championship table, with just 11 points from 10 games. They have yet to win at home this season, and promotion hope from the beginning of the season appears to be disappearing with every passing game.