Terry, 36, is available on a free transfer this summer after ending his 22-year association with Chelsea, and it is understood that a number of English clubs are interested in signing the former England captain.
Di Matteo has branded Terry "a leader in the dressing room", in addition to "the reference for many players", and the 47-year-old has doubted whether Chelsea will ever be able to replace the defender's influence.
"He was a leader in the dressing room, he was the reference point for many players, especially many new players. He represented the true feelings of Chelsea," Di Matteo told beIN Sports.
"It's going to take a bit of time for somebody to step in and take that kind of role. I'm not sure if ever somebody will be able to do so, but certainly taking on the captaincy role and being that important for the team."
Birmingham City are believed to lead the race for Terry, although West Bromwich Albion, Brighton & Hove Albion, Aston Villa and Bournemouth have also been linked with a move.