Sheringham, who moved from Manchester United to Spurs on a free transfer in 2001, the first of four such Bosman moves, said: "It's very dicey to do that. If you go into the last year of your contract and are looking to let your contract run out, but then you get injured in the early part of that season, will you get another club? Will they take a chance on you?"
The former England striker added: "Are clubs going to spend money on someone's who's fit and able or will they take a chance? It's not about money for Michael now, it's about playing games and enjoying being there because he's a good footballer."
Sheringham, speaking at the launch of Wrigley's Extra 90+ campaign, said: "When you do sign these long contracts you don't have the chance to cash in with the big deals but you know you're going to earn money for the next three years and that's a good thing."