Spurs remain embroiled in a relegation battle at the bottom of the Premier League as supporters worry that Championship football is almost certain for the club next season.
Postecoglou guided Spurs back to Europe's premier competition via Europa League glory in 2024-25, but a 17th-placed Premier League finish saw the board sack him without mercy.
Should Tottenham have sacked Postecoglou?
Since then the club have gone through Thomas Frank and have now landed on Roberto De Zerbi who is also struggling.
Sheringham spoke on Tottenham’s managerial troubles which are only growing worse as the club steps closer and closer to relegation.
“Ange Postecoglou must still be sitting at home thinking, ‘how did I lose my Tottenham job?’ I mean, he told everyone he was going to win something in two years, and he did,” Sheringham said.
“They (Tottenham) haven't won something for a long, long time so when he's won the club a trophy, he's somehow lost his job. Why is he still not in charge?
“I understand the league position last season wasn't great, but he put all his eggs in one basket to win something, because he wanted to win something. We all want to win something. I'm still mystified on that decision to replace him to this day.
“It would be very interesting to see where we would be if he had stayed, that’s for sure. I'm not saying that Spurs should go back to him, not now anyway, but we'll never know.”
Spurs are currently stuck in the relegation zone in 18th place with 34 points, two behind West Ham who could be the side to push Tottenham down and make them regret their management decisions even worse.