Gareth Evans earned Macclesfield their first point in six games after cancelling out Martin Gritton's opener.
Spireites striker Gritton, who left Moss Rose in January, fired home from 15 yards after eight minutes.
The Silkmen briefly looked set for another afternoon of woe, but Evans quickly nodded home Ahmed Deen's precise cross from eight yards.
Gritton almost claimed a second before Aaron Downes forced a fine late save, but Macclesfield held on for a point.
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Macclesfield:
Brain, Brisley, Brown, Morgan, Deen, Tolley (Hadfield 80), Bell, Daniel, Yeo (Sinclair 59), Evans, Rooney. Subs Not Used: Walker, Green, Thomas.
Goals: Evans 15.
Chesterfield: Lee, Wilson, Downes, Hall, Robertson, Lowry, Montrose (Kerry 27), Niven (Currie 75), Talbot, Gritton, Lester. Subs Not Used: Austin, Boden, Till.
Goals: Gritton 8.
Att: 2,276
Ref: Carl Boyeson (E Yorkshire).
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