The youth team got their season under way on Saturday away at Scunthorpe United, but despite a strong second half fightback conceded a late penalty in a 3-2 defeat.
Trailing by two goals at half time, a George Milner brace pulled the young Spireites level after the interval and Mark Smith's side then missed a penalty before cruelly giving away a spot kick of their own late on and losing by the odd goal in five.
Despite the defeat, Smith saw enough positive signs to come away from the match with optimism: "We had a slow start and weren't at the standard we're capable of. We changed a few things round at half time, put a few subs on and that seemed to have the desired effect and we got back into the game really quickly.
"We scored two goals in about five minutes and then won a penalty that we missed - then we had a couple of one-on-ones which we couldn't take advantage of.
"Getting the two good goals through George Milner was good, but it was a poor decision by one of our players in the last five minutes that gifted them a penalty and they scored and won the game from that.
"There we some good positives to take from the game and the much better second half performance. I did think we had the best player on the pitch in Derek Daly who had a large part to play in setting up the second goal.
"Last season we got into a situation where we weren't used to getting beaten and it'd be great to get back to that, this was just the first game of the season and we'll look to get to winning this Saturday."