Di Matteo was sacked by Roman Abramovich just hours after the Blues' 3-0 defeat by Italian giants Juventus in the Champions League on Tuesday night, in spite of landing European football's most lucrative prize last season.
The Russian owner backed his new man in the summer, as the likes of Eden Hazard and Oscar arrived in the capital with Atletico Madrid's Colombian superstar Falcao another potential recruit.
But after suffering a similar fate to the Italian, Villas-Boas suggested the Chelsea managerial job has become a poisoned chalice.
"At Chelsea I think another sacking is just like any other day at the office, that's my interpretation," the Spurs boss told Sky Sports.
"Roberto has achieved so much in such a little amount of time. His CV is maybe one of the best in the world now - he has won the Champions League and the FA Cup too."
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Di Matteo has been replaced by former Liverpool boss Rafael Benitez on an interim basis, as Abramovich searches for a permanent replacement.
The Spaniard is the ninth manager in Abramovich's tenure, with Pep Guardiola and even Harry Redknapp thought to be among the favourites for the job.
Villas-Boas endured a torrid time at Stamford Bridge and parted company with the Blues following a league defeat against West Bromwich Albion, but has settled into life well at White Hart Lane.
He added: "It was difficult for Robbie and I wish him well for the rest of his career.
"Regarding the club, it's their decision, it's what they think will take them forward but other than that I can't comment."