Former Chelsea assistant "disappointed but not surprised" by Ancelotti's departure from Stamford Bridge after failing to deliver a trophy this season after last term's double
The Italian was sacked after failing to reclaim the Premier League title; seeing it slip away and into the hands on Manchester United after an indifferent season that included a shocking slump in form around Christmas.
Wilkins was Ancelotti's right-hand man but was fired in November - around the same time the Blues began to struggle in the league - but hinted he could team up with the Italian again.
"To win the double one year and come second the next, it does seem a bit harsh. But football doesn't surprise me any more," he told the BBC.
"He is a good guy and I think he needed to be involved still for them to improve.
"I really feel quite sorry for him - the fact he's not there any more - but I'm sure he'll find another post because he's a good guy and an exceptional coach as well. I'm meeting him next week to see what he wants to do."After a season that saw no return on owner Roman Abramovich's investments - including £50 million for Liverpool Fernando Torres - Wilkins conceded the sacking was not a total surprise.
"It wasn't a big surprise but I'm slightly disappointed for Carlo," he added.
"The owners are looking to win the holy grail - and the Champions League is that as far as Chelsea is concerned.
"The Champions League isn't on their CV. The double, the league and the FA Cup are - only the Champions League is missing and it will be the one Mr Abramovich strives for as long as he's in control of Chelsea.
"Carlo won the Champions League twice as a coach and as a player so the [next] guy is going to be some sort of magician if he comes in and wins it first time.
"They're giving it a good blast to win it - but it's not easy to win it at all."
And on who will replace Ancelotti, Wlkins was left stumped.
He said to Sky Sports News: "I think it (Chelsea's next manager) will be someone from abroad.
"Whether Harry would want to do it or not, I don't know.
He's done a remarkable job with Tottenham in the last couple of years."