Ahead of the winter transfer window swinging open on Friday, Hoddle recalled his work as Blues manager in the transfer market, declaring the arrival of Gullit as the greatest signing of his managerial career.
And he admits it could've been a Dutch double, with Bergkamp available at the time. There was also the chance of bringing Gianfranco Zola earlier to Stamford Bridge before the Blues legend arrived in 1996.
Hoddle, who was in charge at the Bridge from 1993 to 1996, recalled on his podcast, ' The Glenn Hoddle Footy Show': "Funny enough, Zola was one I wanted to bring and it was mooted he could be available, but the money wasn't there at the time.
"Dennis Bergkamp was one we got close to. We nearly did it with Ruud coming at the same time. But the funds just weren't there - it was just out of our reach at that time. But there were few who were on our radar.
"I think looking back if Matthew Harding had been chairman at that moment and he had been willing to put more money in... but I think there was a battle with Ken Bates about who was going to be chairman and I tried to keep out of that political thing. But it could've been a different story.
Gullit was signed by Hoddle in 1995 and would spend three years at Chelsea, eventually becoming player-manager and winning the 1997 FA Cup. Hoddle admits he had identified Gullit for a specific role when first making an approach.
Hoddle said, "The fact he was on a free transfer was quite incredible for the club. To take him there and for the status he had as a player, I think he would be my best signing - especially for no money as well.
"And then I went onto England and he ended up managing the club."
Hoddle says a change in formation he had planned hinged on bringing in a player of Gullit's qualities - which was part of the pitch he made to the Dutchman.
"I wanted to play with three at the back. I had played against him when was a youngster - and he had played as a sweeper then. And I wanted to play him as a sweeper for Chelsea.
"But when he came, we ended up having to play him further up the pitch because we didn't quite have the players around him to play out from the back as I wanted. So we were putting ourselves under immense pressure trying to do that. He understood. I genuinely sold it to Ruud that he would be coming in as a sweeper.
"But money was tight back then and we couldn't go out and buy two centre-backs to play alongside him. I had to work within the squad I had.
"The other players weren't quite comfortable, let's put it that way."
Listen to this week's full episode of 'The Glenn Hoddle Footy Show' - a Tribal Football partner - below:
Click here to visit the full archive of 'The Glenn Hoddle Footy Show'.