One of last season's Spireites is trying to land himself a contract with one of their 2019/20 National League rivals.
Kyel Reid has been on trial with Notts County and Yeovil Town this summer.
The winger has featured in friendlies for both clubs.
A current Chesterfield player, Lee Shaw, is close to securing a loan move to Guiseley.
The Derbyshire Times understands a season-long loan with the National League North side is lined up for the striker.
Another recently departed Spireite, Jerome Binnom-Williams, has spent time with League One club AFC Wimbledon.
The left-back played in the Dons' pre-season friendly with Brentford but was not part of the squad they took to Germany, as part of their preparations for the new season.
Chesterfield filled the left-back berth with the experienced David Buchanan this summer.
There was talk linking ex Town man Dan Jones with a return to the Proact to play in that role, but he was never a target for boss John Sheridan and instead recently joined Cambridge United in League Two.
The Spireites continue to search for attackers and Sheridan wants two more players in.
He'll take another look at Norwich City striker Anthony Spyrou, potentially tomorrow night against Sheffield United.
A family issue kept the teen out of Saturday's game against Rotherham United.
Alex Kiwomya, a name touted by supporters as a potential answer to Chesterfield's pace problem, has not been a target this summer and the attacker is focused on fighting for a place in the Doncaster Rovers team.
Meanwhile Chesterfield are still considering potential exits for another couple of the current squad.
One player to have disappeared from the picture entirely is Ryan Scholes-Beard.
The nephew of England and Manchester United great Paul was involved in pre-season training, with a potential development squad place on offer, but the former Oldham youngster hasn't been given a deal.