Sid Nelson, Liam Ridehalgh, Ollie Banks and David Perkins all started in Tranmere's 1-1 draw with Forest Green.
Banks' screamer of a goal from the first leg proved the difference between the sides and the ex Town midfielder will now feature at Wembley against Newport County, who vanquished Mansfield Town.
The midfielder has played 38 games for Tranmere this season, scoring four goals and picking up 15 yellow cards.
Banks made 81 league appearances as a Spireite during a three-year spell, which was pre-dated by Ridehalgh's pair of loan stays with Chesterfield.
Perkins also spent time on loan with Town, in the 2009/10 season.
Most recently, Nelson was on loan at the Proact from Millwall last season and proved an incredibly popular player with supporters.
Beaten semi-finalists Forest Green also boasted a former Spireite in their starting line-up, in the shape of midfielder Reece Brown, who made two substitute appearances during an unsuccessful loan stint in 2017, while a Birmingham player.
Brown has had an excellent season with the Vegan football club, scoring 11 times in 52 appearances.
Two other former Spireites were Wembley winners at the weekend.
Scott Wiseman and Emmanuel Dieseruvwe were part of the Salford side who beat AFC Fylde 3-0 to book a place in League Two for next season, Dieseruvwe scoring one of the goals.