Chesterfield needed penalties to secure their place in the Northern section final of the Johnstone's Paint Trophy after drawing 1-1 with Oldham Athletic.
Danny Philliskirk had put the home side ahead, but Tendayi Darikwa soon equalised for Chesterfield in the first half, while neither could find a winning goal after the break.
Both sides scored with their first four penalties in the shootout, but Tommy Lee was able to stop the effort from Anton Rodgers to give the visitors the advantage.
Chesterfield will face Fleetwood Town in the final after they knocked out League One side Rotherham United 2-1.
Jeff Hughes had given the home side a first-half lead but Nouha Dicko pulled it back for the visitors shortly after the restart, before Conor McLaughlin tapped in the 70th-minute winner.
Peterborough United thrashed Newport County to make the final of the Southern section of the competition.
Kgosi Ntlhe's left-footed strike put the visitors ahead inside the opening 15 minutes, before stoppage-time efforts from Grant McCann and Nathaniel Mendez-Laing secured the win.
Swindon Town had to rely on penalties to beat Stevenage to set up a meeting with Peterborough in the final.
Nicky Ajose put the home side ahead but Bruno Andrade took the match to a penalty shootout after scoring eight minutes from full time.
Francois Zoko slotted the opening kick of the shootout home for the visitors, but he was the only Stevenage player to score his penalty, allowing Swindon to progress 3-1.
Results in full: Fleetwood Town 2-1 Rotherham United, Oldham Athletic 1-1 Chesterfield (Chesterfield win 6-5 on penalties), Newport County 0-3 Peterborough United, Swindon Town 1-1 Stevenage (Swindon win 3-1 on penalties)
