Now, 28 years on, he will honour the man he calls ‘Mr Tottenham’ when he leads his side out against Fiorentina for the Bill Nicholson Testimonial at the Lane on Wednesday night.
Glenn was just 16 when the revered Bill signed him as an apprentice.
“I remember coming here as a schoolboy when Bill was manager,” said Glenn.
“I trained at the club as an apprentice with the first team when Bill was manager and had my first experiences with the first team at 16, travelling to Red Star Belgrade, all when Bill was manager.
“That was a bit daunting at the time but it was a wonderful experience.
“Obviously the handover as Bill left was just as I was breaking into the team, so I didn’t really play under him as manager.
“I remember instantly when I used to be in the boot room and you saw Bill coming through the other door you used to dread it sometimes because of the respect, you used to dive for cover to get out of the way!
“He would always have a remark for you as well, about how clean your shoes weren’t, or do your tie up, whatever.
“He was a thorough man and a delightful, strong man and a great, great manager.
“If I can come anywhere near what Bill Nicholson achieved for this club, if I can achieve 50 per cent if it, I’ll be a very, very happy man.”
Current boss Glenn is also a very happy man to be involved in such an occasion.
He added: “I’m delighted that the club will honour Bill with a second testimonial and I’m sure his family and close friends will be delighted by that.
“Bill is Mr Tottenham Hotspur and everything this club stands for, Bill was there and put the foundations in.
“He had presence, he knew what he wanted, he knew how his team would function and it was all about the traditions of Tottenham Hotspur Football Club that he helped built.
“He played for the push and run side and then took it on to achieve what he achieved. They are the foundations of the club.
“He was the manager in the most successful period at the club and I’ve always had the highest respect for him, for what he achieved as Tottenham manager.
“I personally feel he should have been knighted by now.”
Glenn, who is talked of in similarly legendary terms as the great man by fans, has followed Bill as a player now in the managerial hotseat at the Lane.
But he admits the hard work starts now.
“I hope I can get anywhere near him,” said Glenn. “I played for the club, like Bill, and I’ve been lucky enough to manage the club.
“What I have to do now is the hardest part — trying to emulate him and try to win as many trophies as Bill did.
“I’m not saying that will be achieved but with hard work it can. Bill was a very dedicated man to this club and I’m delighted to see that the club is treating him with the respect he deserves.”
Glenn Hoddle can still recall how he used to ‘dive for cover’ when the great Bill Nicholson walked into the room.