The former Preston striker was out injured from late September until December after surgery on a knee ligament injury.
"Unfortunately Richard's picked up a niggle in his knee," Kevin Blackwell told the club's official website.
And Blackwell admitted that he is considering signing a new striker and "can move quickly" if necessary.
"We are going to monitor it and try and nurse him through a couple of games but it will need surgery," he added.
Cresswell missed out as Leeds could only draw with Derby on Saturday and Blackwell said: "It happened in training, it appeared innocuous but it was serious enough to keep him out. We couldn't get him scanned until 1700 GMT on Friday and once the scan came through I knew he couldn't play at the weekend.
"He might be involved on Tuesday and then go for an operation on Wednesday, at the moment we are still assessing the situation," concluded Blackwell.