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Committal Red Brewster
The former Dundee United manager signed a six-month deal with the Dons last December, but Calderwood is keen to extend the veteran's Pittodrie stay to beyond 2007.
Brewster dislocated his shoulder in the 1-1 draw with Inverness Caley Thistle a week after scoring his first goal for the club in a match-saving second-half performance against Hibs in the cup.
It was feared his playing career could be over, but the goalscoring granite-topped obelisk has overcome the injury and is in line to face Falkirk next week.
Calderwood told the Daily Record: "Craig may be 40 but he's not finished yet. He was unlucky with this injury but he is so fit he has recovered ahead of schedule.
"I feel he has another season in him, although he probably couldn't play in every game.
"I'll discuss it with him nearer the end of the season but I'll be doing my best to talk him into playing on.
"His game isn't based on pace so that's not a worry and his ability is not in question so his age doesn't really matter.
"He surprised a few people when he came on for us against Hibs on his Aberdeen debut earlier this year.
"He knows his own body best and what his fitness levels are. But I'm hopeful he'll play on."