Caretaker manager Tommy Wright said he was left dumbstruck after Jason Walker's 94th minute wonder goal salvaged a point for York City and prevented his side from registering their first league win of the campaign.
The Spireites took the lead 10 minutes before half-time courtesy of skipper Sam Hird's first goal in over three years, when he prodded home from close range after Marc Richards had twice been denied by Minstermen stopper Michael Ingham. But Gary Mills' side hitback almost immediately through Michael Coulson's deft chip, before Craig Westcarr completed a five-minute scoring spree when he raced clear to slide home.
It looked as though the former Notts County man's second goal in as many games would be enough to take all three points back to Derbyshire, but 28-year-old Walker popped up to slam home at the death and rescue a late point for City.
"I was that gutted I couldn't say anything really, I was dumbstruck and disappointed," the caretaker revealed after the full-time whistle.
"It's frustrating, I thought we'd done enough to win the game. The officials put four minutes on the board and played over four minutes, so I don't understand that really. That's the biggest frustration.
"The goal we conceded was poor as well, we've got to stay disciplined. I've just said to the players in there, that's the difference between a successful side and an average side. 94th minute, or second minute, you've got to defend your goal and we went to sleep," he added.
"They were in their right-back position with a minute to go and we've given them the ball back needlessly. But the players have worked hard for me, they've done well. We played well today. I'm frustrated at this moment in time with such a late equaliser but they're a decent side with a lot of confidence and I thought we came here and played well.
"We had a magnificent support and I think them for that. We filled the whole end and it was great to see and everybody at the club appreciated that."
Chesterfield clinched their first win of the season as they began their quest to become the first club to retain the Johnstone's Paint Trophy with a 2-1 win over League One Oldham on Tuesday night, but the Scotsman made four changes from the side that dispatched of the Latics.
Former Sheffield Wednesday stopper Richard O'Donnell replaced the injured Tommy Lee for his first competitive appearance in a Spireites shirt, while youngster Jacob Hazel replaced Danny Whitaker, who picked up a groin strain in training on Friday morning.
Craig Westcarr also returned to the fray after serving his one-game ban, and Wright was pleased with the efforts with every one of his team.
"I'm pleased with everything O'D did," Wright said.
"He kicked it well, took the pressure off us at times coming for crosses and it's frustrating for him that he wasn't on the winning team. But the players have done really well for me, they've worked their socks off. It's frustrating but we'll kick on.
"My idea with Jacob was because he is naturally left-sided and I wanted that balance. Obviously with Danny getting injured yesterday, that was a problem. But he acquitted himself. He's not a winger, he's a striker but I thought with his pace it would keep the balance. He found it tough at times, but it's a learning curve for him.
"Danny slightly pulled his groin in training yesterday, so he was a big player to lose and so was Tommy, but we dealt with it well and we nearly got three points," he added.
"Everybody worked hard. I thought the two lads in midfield - Mark Allott and Sam Togwell - did well. We changed it a bit because Mark looked a bit heavy legged. We just needed to take a bit extra care with the ball at times, it would have made it easier for us.
"Westy's looked sharp. I had to play him, because he showed in training and at Gillingham that he has got that hunger back in his game and he took his goal very well. We want our centre-halves to score goals, there's no point in them going forward if they don't score goals so it was nice to see Hirdy score. Hopefully there's a few more.
"At this moment in time, i'm absolutely gutted and totally devastated because we were so close to three points.
Tommy's interview ill be available in full on Spireites Player tomorrow morning.