The Blues captain suffered cracked ribs against Benfica last month, but with so many key fixtures coming up, he may have to battle his way through a gruelling schedule
Terry has suffered cracked ribs and was substituted early in the second half of Wednesday's 2-1 win over Benfica as he was finding it hard to breathe.
He is expected to be rested for Saturday's clash with Wigan, but Di Matteo admitted he may have to gamble on his skipper's fitness.
He told reporters: "With a rib injury, it needs time to heal. Every time you get a knock, you probably go a step back.
“We’re just trying to manage the injury at the moment and we’ll just have to see how quickly he can recover.
“It’s one of those injuries that are difficult to deal with because there’s not much you can do. It’s in a position where it’s difficult to make it better.
“We need to just deal with the pain level and give him a bit of time to recover.”
Amidst the battle for a top-four finish, the Blues face Spurs in the FA Cup next week, before a Champions League semi-final against Barcelona.
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The Wembley date with Harry Redknapp's men is scheduled to kick off at 6pm, just three days prior to the meeting with the Spaniards, a move that has not gone down well at Chelsea.
"I’m very disappointed that common sense hasn’t prevailed in this," Di Matteo continued.
“Obviously, they didn’t take into consideration anything that we said. Barca will have one more day to recover than us and it might give them a little advantage.”
Barcelona could be handed even more of an advantage if the Spanish authorities agree to bring forward their La Liga clash with Real Madrid.
The Italian added: “Other federations are very helpful, but the FA haven't seemed very helpful in our case.”