Winks and Dier have been picked in midfield regularly this term, with both Moussa Dembele and Victor Wanyama struggling with injury.
And Le Tissier, ultimately, feels that Tottenham’s lack of depth could harm them in the race for a Champions League spot.
He said: “Tottenham have had a couple of setbacks and are missing Toby Alderweireld and Victor Wanyama. I'm not convinced by Eric Dier and Harry Winks as a central-midfield pairing and I'd change my mind about them being in the top four if you played those two for the rest of the season.
“Winks has a lot to learn and flatters to deceive in my opinion in terms of his impact on a game compared to Mousa Dembele.”
Winks has generally impressed since breaking into Tottenham’s team, and his form was even rewarded by Gareth Southgate recently, with the youngster earning international recognition with England.
Dembele is currently fit and available, but the Belgian international struggles to play 90 minutes due to his persistent fitness problems.
Spurs have slipped out of the top four recently, and currently sit in fifth place in the Premier League table.
Tottenham are next in action later this evening, when they take on Leicester City at the King Power Stadium.