Chesterfield chalked up their first victory of the season but were made to work hard by Macclesfield who should have taken the tie into extra time After going two goals behind in the first 15 minutes the Silkmen had enough chances to draw level but could not find a decent finish in the second half.
Chesterfield looked to be on course for an easy passage when Jamie Cade got on the end of a left-wing cross from Alan O'Hare as the visitors froze.
Carl Muggleton twice had to make smart saves before further bad defending allowed Marvin Robinson to rifle a right foot shot past Steve Wilson from 15 yards.
But the visitors got a lifeline within 60 seconds when Danny Adams arrived at the back post to sweep in a low cross.
The second half belonged to the visitors and they should have taken the game into extra time but the quality of finishing left a lot to be desired.
First Matthew Tipton side-footed wide from eight yards when Martin Carruthers drove the ball in from the right and he failed to take advantage of another inviting opening in the 59th minute.
His first effort was blocked and he drove the rebound against a post with the home defence wide-open, and the Spireites lived to make it into the second round.