The Spireites are looking to build momentum heading into the 2023-24 campaign, in which they will be aiming to gain promotion from the National League, while the visitors are in need of match practice ahead of their return to the Championship next season.
Match preview
Chesterfield came agonisingly close to winning the National League playoff final at Wembley last season, losing to Notts County on penalties, with the game all square at 2-2 after extra time.
Of course, the Spireites will be wounded by missing out on promotion in that fashion, but now they must make sure they are ready to go again next season, and they could challenge for top spot this time around.
Paul Cook remains in charge at the Technique Stadium, with the manager already overseeing two pre-season games, and his side ran out comfortable winners in the first of those, defeating Matlock 9-0.
Will Grigg notched his first two goals in a Chesterfield shirt in that encounter, and the Spireites' new striker has since gone on to find the back of the net in the 5-1 victory against Alfreton on Saturday afternoon.
Having faced weaker opposition in their first two friendly matches, Cook's side are now preparing for their first real test of pre-season, against a Sheffield Wednesday side that managed to seal promotion back to the Championship last season.
Indeed, Wednesday brought their two-year stint in League One to an end in the previous campaign, but they did not make it easy for themselves, missing out on automatic promotion by two points after going on a six-game winless run starting in March.
Things went from bad to worse for the Owls when they lost 4-0 away at Peterborough United in the first leg of their playoff semi-final, but they managed to turn the game on its head in the second leg, before Josh Windass's late winner secured a win against Barnsley at Wembley.
Despite leading his side to a fairytale promotion at Wembley, Darren Moore has since left Sheffield Wednesday by mutual consent, with the club recently appointing former Watford manager Xisco Munoz as his successor.
Owls fans had their first chance to see the new manager in the dugout when they travelled to York City on Saturday afternoon, but Munoz was unable to get his first win on the board, with Windass's goal being cancelled out by a second-half Finlay Barnes effort.
Chesterfield pre-season form:
Sheffield Wednesday pre-season form:
Team News
Chesterfield fans will be excited to see Grigg in action at the Technique Stadium for the first time, having joined from MK Dons for an undisclosed fee last month, and the Northern Irishman could partner Joe Quigley in attack.
Other new arrivals for the Spireites include Harry Tyrer, who is set to start between the sticks, and Tom Naylor, with the former Wigan Athletic man poised to start in central midfield.
Sheffield Wednesday's only acquisition so far this summer is left-back Reece James, who joined from Blackpool for an undisclosed fee last month, and the 29-year-old is likely to start, having been named in the starting lineup last time out.
It would not be a surprise if Munoz hands starts to some young players, with 20-year-old forward Luke Cook in line for another run out, while midfielder Sean Fusire may also be given some game time.
Chesterfield possible starting lineup:
Tyrer; Grimes, Maguire, King, Williams; Naylor, Banks, Mandeville, Colclough; Quigley, Grigg
Sheffield Wednesday possible starting lineup:
Dawson; Brennan, Famewo, Iorfa, James; Johnson, Windass, Bannan, Bakinson; Gregory, Cook
We say: Chesterfield 0-2 Sheffield Wednesday
Wednesday did not manage to record a win against York City last time out, but the truth is it matters very little, as the most important thing in pre-season is implementing new tactics, and getting players up to speed.
As such, the result will depend on the quality of the side Munoz chooses to field, with some youngsters likely to be given a chance to impress, but the Owls should still manage to pick up a relatively comfortable victory.