Clive Allen believes the Italian will be the man to take charge at White Hart Lane this summer as Louis van Gaal looks set to move to Manchester United
Sherwood, who signed an 18-month deal to replace Andre Villas-Boas midway through the season, is widely expected to leave his post at the end of the current campaign, with Netherlands coach Louis van Gaal and Southampton boss Mauricio Pochettino among the candidates linked with the role.
However, with Van Gaal looking likely to take over at Manchester United in the coming weeks, Allen - who played more than 100 games for Spurs before caretaker spells in charge in 2007 and 2008 - believes Ancelotti could make a shock switch from Santiago Bernabeu to north London in the summer.
"If I was a betting man I'd have my money on Carlo Ancelotti," he told talkSPORT when asked who could take over from Sherwood.
"There won't be just the one option, because if was Van Gaal was on their list, that's gone now, his move to Man United looks to be done and he's been very clever with his recent comments.
"I think they'd look at someone like Pochettino too."
Ancelotti has also been linked with a possible move to United this summer, though the Italian himself stressed on Monday he wants to remain with Madrid "for a long time" as he attempts to guide them past Bayern Munich in the Champions League semi-finals.