Striker Eoin Doyle scored twice but was left distraught as the Spireites conceded a 94th goal to lose 3-2 at Bristol City.
September's League One player of the month scored a first half penalty and then a second half poachers goal to twice level proceedings at Ashton Gate.
However, with the visitors pushing for a winner of their own the Robins broke and Wes Burns finished to settle the contest in the home side's favour.
After the match Doyle was finding the result tough to get his head around.
He said: "It's very difficult to take at the minute, it's a bit heartbreaking. We were well in the game and we fought back twice like that, and we could have pipped it ourselves at the end.
"It could have gone either way and unfortunately it went their way."
"It's down in the dressing room, it is down. To come back twice then concede in the 94th minute is hard to take."
At 2-2 in the closing stages the Spireites looked the ones more likely to grab a winner, making the eventual loss all the more gut-wrenching.
Doyle said: "Even when the board went up and it said four minutes extra, we were the team that kept pushing, trying to go and maybe get the winner.
"Obviously it wasn't to be and they managed to catch us on the break. They've put a good ball in and they've managed to score from it. It's a bit heartbreaking."
Despite the defeat, Chesterfield showed again how at home they are at League One level, and Doyle explained how the team will take on board the result.
He said: "We want to be up there with them and this puts a bit of a dent in that. I think there are a few good points to take away from today, all we can do now is put this behind us and prepare for next week."