The Spireites’ FA Youth Cup campaign gets underway tomorrow, with the youth team playing Notts County in the first round of this year's competition at the Proact, 7pm.
It will be a chance for the young players at the club to get a break from normal league proceedings as they go in search of a cup run.
Not since the 1950s have the club been able to get close to winning it however. Chesterfield's only appearance in the final was in the 1955/56 season, as they were beaten by Manchester United. England legend Gordan Banks was the Spireites goalkeeper at the time, but he couldn't prevent his side from defeat over two legs.
United beat Chesterfield 3-2 in the first leg, with a certain Bobby Charlton scoring on the day.
Despite coming back from 3-0 down in that tie the Spireites couldn’t turn things around and drew 1-1 at Saltergate in the second leg.
In more recent times though, the youth team have gone as far as the fourth round. That was in the 2014/15 season, but they were knocked out by Leicester City in a 1-0 defeat at the King Power Stadium. Along the way they beat Stocksbridge Park Steels, AFC Fylde and Aston Villa, with a team captained by Laurence Maguire.
In the 2015/16 season Chesterfield exited the Youth Cup to Sheffield United, losing 3-0 in the second round and the Spireites were also knocked out in the same round last season.
They succumbed to Carlisle after extra time. Dylan Hand was the Chesterfield scorer, in a side that contained Joe Rowley who is currently enjoying a run in the first team and Charlie Wakefield.
The competition has often served as a launch pad for a host of players with Rowley, Wakefield and Maguire the latest names to go from FA Youth Cup appearances to first team action.
If the team is to progress beyond the first round on this occasion, then Port Vale await them in round two.