The Spireites lost 1-0 at the Bescot Stadium despite dominating throughout in terms of possession.
The goal came just before the interval at a time when the Spireites looked to have the edge, instead they fell to a well-taken strike from Daniel Kanu, who used his speed and strength to burst through before powering home.
Apart from a late flurry towards the end of the second half the Walsall defence dealt well with the limited threat and saw the game out.
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Paul Cook made two changes from the previous league game, in which the Spireites recovered from a two-goal deficit to draw with Crawley Town. In came Tom Naylor and Dilan Markanday while Dylan Duffy and Matt Dibley-Dias missed out through injury.
Manchester City loanee Will Dickson featured for the first time, on the bench. For the home side, not one of their starting line-up took part in the play-offs last season, such has been their pre-season shake-up.
Another huge following greeted the Spireites onto the pitch. The toss of the coin decided that they’d be kicking towards their supporters.
Walsall’s Derbyshire-born captain, Aden Flint, got his head to a second-minute corner from the left but could only direct it wide of the right upright.
The swirling wind was making it hard to predict the path of the ball in the air. Two minutes later, Chey Dunkley also played safe by conceding another flag kick.
Just before the quarter-hour mark Armando Dobra took a knock and play was halted. He was quickly back in action but picked up a yellow card a few minutes later when the referee decided his claim for a foul wasn’t warranted.
After 27 minutes, Dobra was bundled over just outside the area; Ronan Darcy decided to try his luck; his angled hit flew narrowly over the bar.
Walsall gained another corner on the half-hour – Charlie Lakin connected but his effort flew wide of the left upright.
The Spireites broke well on the left and Lewis Gordon hit for goal from close to the bye-line, forcing Myles Roberts to clear with his feet, moments later Ryan Finnigan had no option but to concede another corner from Darcy’s ball in.
In the next move Daley-Campbell’s close-range effort forced a hasty kick to safety from the home keeper.
In the 43rd minute, the Saddlers broke the deadlock. Kanu burst down the right, evaded Kyle McFadzean’s challenge and continued his run before blasting firmly home from inside the area.
Three minutes were added at the end of half. Walsall gained another corner but again the wind took hold and the ball blew to safety just as the referee signalled the interval.
The scoreline was hard to take at half-times as, having weathered the early storm, the Spireites had bossed the 20 minutes before the well-taken strike gave the home side an advantage at the break.
Dobra kicked off to start the second period as the Spireites looked to get back into the game. The first chance of the half came when Lakin received on the left and hit strongly from inside the area, forcing Spireites’ keeper Hemming to clear with both feet.
Good work by Dobra saw the ball fall to Markanday, wide-right, who decided to go for goal but his effort was high and wayward.
Connor Barrett picked up a yellow after Lewis Gordon was hurt while several players challenged for the loose ball.
In the 67th minute Walsall went down to ten men after Lakin picked up his second yellow card for a foul on Tom Naylor.
Five minutes later Paul Cook made a triple change as Will Grigg, Devan Taunton and Adam Lewis replaced Darcy, Daley-Campbell and Gordon.
Chesterfield increased their share of possession while the home side was happy to defend deep and break when possible.
Cook made his final two changes as Liam Mandeville and Dickson entered play.
Substitute Lewis floated over a long ball from the left that eluded everyone and flew to safety.
In added time Stirk launched a great ball to the far post, Dobra rose to meet it but glanced his header wide of the upright.
With just one minute of the six added minutes remaining Chesterfield should have levelled after Dunkley headed Tanton’s cross from the right agonisingly over the bar. No further chances emerged and the Spireites fell to their fourth consecutive league defeat against the Saddlers.
Chesterfield: Hemming, Naylor, Gordon (Lewis 72), McFadzean, Dunkley, Stirk, Bonis (Mandeville 83), Dobra, Daley-Campbell (Taunton 72), Markanday (Dickson 83), Darcy (Grigg 72)
Subs not used: Boot, Fleck
Referee: Zac Kennard-Kettle
Attendance: 6,695
