The Spireites came from behind to draw 1-1 with Manchester City U21 in their opening Bristol Street Motors Trophy tie and then won the resulting penalty shoot-out 4-2 to claim an extra point.
Jacob Wright put the visitors ahead before substitute Darren Oldaker equalised soon after coming on.
Academy graduate Ashton Rinaldo made his first competitive appearance in goal and Paul Cook also handed Kane Drummond and Harvey Araujo their first starts.
Mike Jones had an early shot blocked before the defence managed to scramble the ball away.
Joe Quigley tried a shot from the edge of the area which was well saved by Jack Wint.
City went close to taking the lead when Nico O’Reilly’s chip from inside the area clipped the bar before being cleared.
Shortly before the break, Drummond’s curling effort went agonisingly wide.
Drummond also threatened soon after the re-start, going past a defender before seeing his shot deflected over.
The opening goal came in the 52nd minute when Wright found the net with a free-kick.
A triple substitution came in the 74th minute with Vontae Daley-Campbell, Connor Cook and Oldaker replacing Bailey Hobson, Quigley and Jones.
Oldaker soon made his mark, equalising in the 79th minute with a free-kick, floating the ball over the defensive wall and into the roof of the net.
In the shoot-out, Oldaker, Drummond, Cook and Berry converted their penalties. Rinaldo saved City’s first spot-kick.
Spireites: Rinaldo, Horton, Grimes, Araujo, Jacobs (Berry 83), Williams, Hobson (Daley-Campbell 74), Akinola (Mohiuddin 83), Quigley (Cook 74), Drummond, Jones (Oldaker 75)
Attendance: 2,446
