Despite overseeing Chelsea's inaugural Champions League triumph — when they became the first London club to win the European Cup — in a penalty shoot-out over Bayern Munich last season and also bringing the FA Cup to Stamford Bridge, di Matteo was sacked Wednesday.
Only appointed on a permanent basis in June, di Matteo was dismissed fewer than 24 hours after Tuesday's 3-0 defeat by Juventus in Turin left Chelsea poised to become the first Champions League winners to be knocked out in the group phase the following season.
Di Matteo, 42, is the seventh coach to have been sacked by owner Roman Abramovich since the Russian billionaire bought the club in 2003.
"If you win something at Chelsea you get sacked," Gullit, Chelsea manager from 1996 to 1998 when Italy midfielder di Matteo was still a player with the club, told Sky Sports.
"I'm very sad for Robbie," the Dutch great added. "I had a feeling when they won the Champions League they maybe had someone else in the frame. That's why they took so long over his contract."
And Gullit said he felt it was possible former Chelsea boss Jose Mourinho, once sacked by Abramovich, could yet return to Stamford Bridge.
"I always had the feeling Mourinho was always in the frame all the time."
Meanwhile Manchester United defender Rio Ferdinand accused Chelsea of "madness" in sacking di Matteo, and contrasted the situation with that at his own club, where Alex Ferguson has been the manager for 26 years.
"Wow, Chelsea have sacked their manager!!," Ferdinand told Twitter.
"I'm a bit late I know but its a madness.
"The stability at our club is something our manager rarely gets praise for…don't under estimate that. £LambChopped."
Alan Pardew, manager of Chelsea's Premier League rivals Newcastle, was equally stunned by di Matteo's departure.
"I'm astonished, really," said Pardew, who in September was given a new eight-year contract by Newcastle — a remarkably lengthy deal by current standards in English football.
"It just goes to show you how precarious we are as Premier League managers, and you can't take anything for granted.
"The shock that should be there for the fans and the media should sound something to the owner of that football club because I don't know if that's the ninth manager or whatever it is in so many short years. It's just not fair.
"As far as I am concerned, he has done absolutely nothing wrong. His philosophy was to perhaps change the look of the team, which he has tried to do — that doesn't happen overnight — and he's won two competitions in less than a year, so it's unbelievable.
"He should walk straight into another job — probably at someone else's misfortune, unfortunately."
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