Ahead of the Spireites' trip to Oakwell we take a look at a man who has played for both clubs - as well as taking charge of both teams from the touchline.
Current Spireites boss Danny Wilson is in his first season at the Proact, however he has been on the managerial scene since 1994. He has had spells at Sheffield Wednesday, Bristol City, MK Dons, Hartlepool United, Sheffield United and two separate spells at this weekend’s opponents Barnsley.
Wilson also spent time as a player at both Chesterfield and Barnsley as well as Bury, Nottingham Forest, Scunthorpe United, Brighton, Luton Town, Sheffield Wednesday and his hometown club Wigan Athletic.
Starting his career at Wigan before moving to Bury, Wilson caught the eye of Chesterfield boss Frank Barlow who brought him to Saltergate. Wilson appeared for the Spireites on 100 occasions and found the net 13 times.
After playing for Forest, Brighton he went on to win the League Cup with both Luton and Sheffield Wednesday before moving to Barnsley. Wilson appeared 77 times for the Tykes scoring on two occasions.
It was at Barnsley where Wilson would make the transition from player to manager as Viv Anderson left and Wilson was named player-manager. After two seasons of missing out on the play-offs in Division One he managed to guide his side to 2nd place, meaning they were promoted to the Premier League for the first time.
However after relegation back down from the Premier League Wilson went to another former club, Sheffield Wednesday. He would also manage Sheffield United later as well as multiple other clubs, winning the Football League Trophy with Bristol City and earning promotion from League Two with Hartlepool United.
All this before joining Barnsley for a second stint in charge in 2013. He joined the Tykes as they were bottom of the Championship in late 2013 however he couldn’t prevent relegation to League One.
Ten months after parting company with the Tykes, Wilson would be named as the Chesterfield boss on Christmas Eve.
Since arriving at the Proact he has managed to steer the club away from the drop zone all starting with an impressive 7-1 victory over Shrewsbury Town in his opening game.
Wilson will be remembered by Barnsley fans as the man who took them to the Premier League. As a player he will be remembered as a tough tackling midfielder who served for both sides.
However, his legacy as Chesterfield manager is still to be decided - but keeping the Spireites up this season would certainly go a long way.