Villa took four points and did not concede a goal in two games against Boro earlier in the campaign.
The teams now meet at the Riverside Stadium on Saturday for the first-leg of a play-off semi-final, with the return at Villa Park a week tomorrow.
Villa won 1-0 on Teeside back in December but assistant boss Calderwood believes what happened then has no bearing on the pivotal showdown to come.
“I have been in this situation where we have been beaten twice by teams during the season and then we have beaten them in the play-offs,” he said.
“Our belief is we can win and get through.
“Everyone has that attitude.
“We are not thinking a play-off semi-final is the limit of our success.
“It is back to work tomorrow and look forward to what could be a tremendous ten days. We hope to progress it further forward in the month.”
Middlesbrough were only confirmed as Villa’s opponents in the dying seconds of yesterday’s final round of league fixtures, with a 2-2 draw at Ipswich seeing Tony Pulis’s team pip Derby to fifth place.
A much-changed Villa team were meanwhile beaten 1-0 at Millwall.
“At one moment it was Derby, the next they (Boro) have scored,” said Calderwood. “In our heads it was always going to be Boro.
“They will be ready for us and we will certainly be ready for them.
“The atmosphere at Millwall will be akin to what we will find in the semi-final. We will be going along at that level of heightened atmosphere and it may help us.
He added: “Of course you want to be finished. But we are not. We knew that.
“We are well programmed in for it and just have to get the balance right this week in training, to have enough energy and resources to get through two games. We have to handle both occasions and look forward to it.”