Jose Mourinho's expensively-assembled side have not won the famous competition under the Portuguese manager's reign - despite the luck of the draw often pairing them with lower division team, including Scunthorpe in 2004.
The London side often concede against team from leagues below them, but they have yet to suffer an upset while under Mourinho.
And although Calderwood is not going to overplay his side's chances of changing that statistic, he is hoping to pick up some tips from the way his Champions League-winning counterpart works.
"I have never met Mourinho and I do not think you should style yourself on anyone else, but my coaching staff and I - as well as the players - will take a lot of things out of this weekend's experience," said the Forest boss.
"Just to try to understand Mourinho and Chelsea's mentality and to pick up bits and pieces down there will be very valuable.
"Jose has his own style but what he has done is back up what he has said with fantastic success, you have obviously got to have total respect for the man."