And Calderwood knows better than most the danger Crawford poses having managed him at Dunfermline and Aberdeen.
Despite now being in the twilight of his career, the Dons boss says his defence will still have to be on their toes to keep the 35-year-old at bay.
"You never lose that touch in front of goal," said Calderwood. "Craig Brewster still has it at 42 and Stevie still has it now. He has a magnificent football brain and he is a great professional."
Calderwood has a selection headache for the match as Zander Diamond, Gary McDonald, Darren Mackie, Andrew Considine and Jamie Smith will all miss the cup tie through injury.
However the Dons will remain firm favourites to progress into the next round at the expense of their visitors from the Second Division.
But after losing 4-3 to Queen of the South in last season's Scottish Cup semi-final, Calderwood has warned his players not to make the same mistake of underestimating lower league opposition.
"It will be a long time before the pain of that defeat to Queen of the South ever goes away," said Calderwood.
"We know this match is East Fife's cup final and I expect them to make it very difficult for us. They were champions of their league last year so they know what it is like to be successful. We have already had a difficult game against Alloa this season and we know East Fife will make it a real test for us."
The Dons will be spurred on by the incentive of an away tie against Airdrie United or Dunfermline in the quarter-finals of the competition.
Calderwood says it is important for his side to get in front early in the tie against East Fife to prevent a tense evening at Pittodrie.
"It becomes more difficult for you the longer you go without scoring," the Dons boss said. "They become more confident and your supporters start to become restless. It would be nice to have the game wrapped up by half-time but we know how these games can go."
A win would also set the Dons up nicely for their crunch Scottish Premier League encounter with Dundee United this weekend.
"It is a massive week for us but that just means we are involved in everything and that is where we want to be," said Calderwood. "It was disappointing to lose to Hearts at the weekend but hopefully we can go on and win these two games.