Macclesfield overcame their LDV Vans Trophy jinx by finally winning at their eighth attempt against Chesterfield.
Matthew Tipton made amends for an earlier miss when he took a neat pass from John Parkin to thunder a low left-foot shot past keeper Carl Muggleton.
The Spireites equalised when on-loan winger Jamal Campbell-Ryce darted through score from 20 yards.
Macclesfield's John Miles then passed to Danny Whitaker, who crashed a 20-yard shot in off the crossbar.
Macclesfield: Fettis, Briscoe, Welch, Barras, Harsley, Widdrington (Carragher 75), Whitaker, Bailey (Potter 35), Miles, Tipton (Sheron 72), Parkin.
Subs Not Used: Wilson, Swadi Fayadh.
Goals: Tipton 23, Whitaker 63.
Chesterfield: Muggleton, Bailey, Downes, Blatherwick, O'Hare, Smith, Davies, Hudson, Campbell-Ryce (De Bolla 78), Allott, Allison.
Subs Not Used: Nicholson, Richmond, Evatt, Michael Fox.
Booked: Allott, Campbell-Ryce.
Goals: Campbell-Ryce 58.
Ref: M Fletcher (Worcestershire).