The Czech international keeper turned up at Stamford Bridge in the summer of 2004 to find the boss who had splashed out £7million for him had been axed.
Since then six different managers have arrived - and five have left.
The Blues' Player of the Year Cech said: "At Chelsea, one day you have a manager - the next day you have someone else.
"One day you play for Chelsea, next day you are somewhere else. So you learn very quickly that everything can change very suddenly.
"It was a strange situation with Claudio. He was the manager who bought me for Chelsea.
"It was February 2004 and it was agreed I would join at the end of the season. But when I flew to London to sign the deal Chelsea were playing away and he was not there. And when the summer came he was not there again - he had been sacked. So the first time I met him was when he came back to Chelsea last season to monitor our training.
"It was funny. I said to him 'Finally it's nice to meet you! It's only been seven years!' But that's how football is.
"When I signed for Rennes I had two bosses in my first season - the one who signed me was sacked after eight games.
"I came back from international duty and there was another guy in charge.
"I was much younger then and thought 'Oh no, a new manager! This will be really tough'.
"But these days I'm used to it. And although we keep changing managers it's always me in goal and I'm proud of that."
Bosses have come and gone at the Bridge but 29-year-old Cech has been a constant - the first choice of Mourinho, Grant, Scolari, Hiddink and Ancelotti.
But what now under Villas-Boas?
Cech said: "No matter who the boss is, you just have to concentrate on doing things right. It's the quality of the work you do on the pitch and in training that determines whether the manager keeps you in or out. It's down to you - not him.
"I'm proud of my Chelsea records; most clean sheets in a season, fewest goals conceded and especially for achieving 100 clean sheets in 180 games.
"That's even better than the great Peter Schmeichel, who took 212 games.
"And, thankfully, I've managed to please all of my Chelsea managers."
Cech is also hoping Villas-Boas will be in charge for a long time after a succession of false managerial dawns.
The keeper added: "First there was Jose Mourinho and we had a lot of success but that came to a sudden end.
"When Phil Scolari came everyone thought we would keep the manager for years. But that didn't work out at all.
"Guus Hiddink did well but couldn't stay because he was manager of Russia.
"When Carlo Ancelotti was announced everyone again said we had the manager to lead us a long time."
Cech was also quick to quash talk of factions in the dressing room last term, reported rifts that ensured a trophy-less season which cost Ancelotti his job.
He added: "I'd be disappointed if players were happy they were not playing. We want everyone competing hard.
"And we'll need to be at our best again next season. It's not just Manchester United we need to match, there's City, Arsenal and Spurs. And I have a feeling Liverpool will be a force again.
"It's going to be an exciting season."
But maybe the most exciting thing will be keeping the manager for once.