Goals from Sylvan Ebanks-Blake and Kristian Dennis gave the Spireites a winning start in the Checkatrade trophy, with a 2-1 Wolves success.
Ebanks-Blake put the hosts ahead midway through the first half with a poacher's finish, with Ethan Ebanks-Landell being shown a straight red card before the interval.
Second half and Christian Herc pulled Wolves level, but within a minute substitute Dennis restored the Chesterfield lead; the home side able to hold on this time with Wolves missing an injury-time penalty.
It was by no means simple for the Spireites as Wolves piled all sorts of pressure on them in the last ten minutes when they hit the post and missed a penalty.
Ebanks-Blake, playing against his former club, was making his first start of the season and was looking to stake a claim for a first-team place and did his chances the power of good on 24 minutes when he fired in from close range after Jon Nolan’s corner was headed back by Ian Evatt.
It got worse for Wolves when they were then reduced to ten men four minutes later after Ebanks-Landell flew into a challenge on Nolan who had beaten him to a loose ball. The referee didn’t hesitate to brandish the red card and there were few complaints from Wolves.
Despite the man advantage, it remained a close affair and Wolves saw plenty of the ball in the second half.
Ebanks-Blake threatened with a close-range volley before Wolves equalised in the 74th minute thanks to a wonderful 25-yard curler from Herc. The Spireites made the perfect response and regained the lead 90 seconds later thanks to Dennis’ deflected strike from just outside the box, his first goal for the club.
Dion Donohue had a good chance to put the game when he fired in a low shot that fizzed wide of the post.
Lloyd Allinson, making his Spireites debut, pulled off a fine save to deny substitute Aaron Collins, who tried to squeeze the ball in from a tight angle. Wolves then hit a post from the resulting corner, with Collins getting the final touch.
It was Collins who was causing the Spireites all sorts of problems and in added time he found himself free in the area before being brought down and the referee pointed to the spot. Collins stepped up to take the penalty, but Allinson's left-hand post came to Chesterfield's rescue as they hung on to claim all three points.
Chesterfield: Allinson (gk) - Donohue, Evatt (c), Raglan, Graham - Gardner, Dimaio, Nolan (Maguire 80'), Ariyibi (Daly 46') - Simons (Dennis 61'), Ebanks-Blake
Subs not used: Fulton (gk), Beesley, German, Ofoegbu
Wolverhampton Wanderers: Flatt (gk) - Simpson, O'Hanlon, Ebanks-Landell, Johnson, Gibbs-White, Herc, Randall, Enobakhare (Collins 82'), Ronan (c), Dicko (Wilson 65')
Subs not used: Odoffin, Burgoyne, Hayden, Leak, McKenna
Chesterfield: Ebanks-Blake 24', Dennis 76'
Wolverhampton Wanderers: Herc 74'
Attendance: 950 (120 away fans)