And after seeing Premier League side West Brom humbled by the Championship's Burnley in the FA Cup, Calderwood has vowed to name his best XI to face the Second Division outfit.
"We are not going to take any chances," he said.
"We will pick the strongest team that we think can win that game. We aren't good enough to underestimate anybody.
"I understand that West Brom played a few players that hadn't been playing regularly for them the other night. We want to win this match so we need all of our best players on the park."
The Dons last lifted the Scottish Cup trophy in 1990 thanks to a dramatic 9-8 penalty shoot-out win over Celtic.
Calderwood admits ending Aberdeen's 19 years of Scottish Cup misery since that triumph is at the top of his agenda.
"Finishing third in the league was always the aim for me because it shows you have been consistent over the course of the season," he said.
"But when you know it is nine years since you have been in a final and 19 years since you have won the Scottish Cup then I think the preference would be to win the Scottish Cup. We have every chance of going on and doing it.
"I have had some great times at Aberdeen but that would be the icing on the cake. It would be absolutely fabulous and the supporters - whether they like you or not - would never forget you if you did that."
Calderwood will recognise a few familiar faces in the East Fife team this weekend who will be doing their utmost to knock their old boss out of the cup.
He said: "I have had Steve Crawford at two different clubs and he is a fabulous lad and a great guy to work with.
"When he was up front with Craig Brewster I thought they were phenomenal together.
"I have also managed Chris Templeman and Greig McDonald and I know they will also be out there looking to do well."
Calderwood added that he would not be taking the Second Division side lightly after getting some words of warning from former Dundee United boss Jim McLean.
He said: "I went down to watch East Fife play Arbroath a couple of weeks ago and Jim McLean was there with his wife. He spoke very highly of them and was praising their manager David Baikie.
"For a man of that quality and experience to say that about somebody is enough for me. We have been well warned."