While Spurs are struggling to get out of the bottom half of the Premier League table, the Londoners have a Europa League quarterfinal showdown with Eintracht Frankfurt.
And Sherwood is convinced Tottenham are capable of winning the title this season.
Speaking to Tribalfootball on behalf of Norsk Poker, Sherwood said: "Yeah do I think this is a real chance. It's been a poor season you have to admit, but it can be an absolutely magnificent, the best season Spurs have ever had if they win Europa League because they would win a trophy the fans are desperate to win.
"Look at the Newcastle fans, you saw their reaction yesterday. They will not be going to work for like two weeks! It's a bank holiday today in Newcastle.
"That would happen in Tottenham. That reaction is what Tottenham fans want. They will be watching that yesterday and say, please let that be us in May. Now, it's going to be a lot tougher from here on in. I think they've had an easy ride. I mean, it hasn't looked easy and I don't want to be disrespectful to any teams, but with Tottenham's squad of players, and I know they've had injuries, they should not be where they are at the moment."
While many Spurs fans are calling for Postecoglou to go, particularly after defeat at Fulham on the weekend, Sherwood insists the Australian can still change everything around.
Sherwood added, "Now Ange Postecoglou has got an opportunity now to be a hero at that football club. He can win this trophy and I think they're capable of winning it and then they qualify for the Champions League next year and everything is rosy in the garden.
"He can start again and build and get some more finances and hopefully you're a Champions League team and you can recruit better players and then yeah, it sounds easy, everything is easy talking about it but you do still keep faith."