Glenn managed the Blues from 1993 to 1996, a time when the refurbishment of Stamford Bridge was in its early stages and cash to spend on players certainly had its limits.
It is all a far cry from money invested in players this summer as new owner Roman Abramovich seeks to put Chelsea on Europe's top table.
"It is an incredible change when I think back to the early days when I was there - the old stadium with a dog track round it," smiled Glenn. "It was very difficult to get the atmosphere then that they get now.
"The training ground wasn't up to much - I came from Swindon and there was better facilities there.
"To see what has happened there, what has evolved over a period of time, is quite amazing.
"Add to all that what has changed in the last three or four months alone - the amount of money that has been spent and where they are setting their sights.
"It is wonderful for Chelsea Football Club but, when you compare it with when I walked in there, it is a miracle."
Glenn acknowledges that Chelsea now possess a depth of squad to cope with virtually any eventuality, but says Claudio Ranieri does need time to bed players in.
"They are probably the only club in the world at the moment that have two teams of almost equal stature on their books. The only other manager, possibly, in the world who could do that is the Brazilian manager because they always have such a choice.
"I still suspect, like Claudio has been saying, that he will need time to gel it all together."
Glenn Hoddle recalled an old ground with a dog track round it while assessing when asked about the transformation of Saturday's opponents Chelsea.