The young Spireites lost 3-0 to Port Vale on Friday lunch time in the Youth Alliance Cup as they extended their winless run to five games.
The result means that the Spireites are now knocked-out of the cup competition.
Vale were ahead at the break after scoring from a set piece, and capitalised with two further goals after the break to confirm their win at Clay Cross.
"We are struggling at the moment," said academy manager Mark Smith. "I'm a little bit disappointed with the players who are now getting the chance to play but aren't taking the opportunities to try and force their way into the team and then stay there.
"We're not scoring enough goals, not taking enough chances and then over the last two games the defending, which has generally been quite solid all season, seems to have gone AWOL a little bit.
"We concede silly goals, on Friday one was from a freekick where the wall didn't protect the goal properly and then we conceded a second goal after we had a freekick in our half but we were beaten by a clearance which put one of their players in on goal.
"We weren't at our best by a long chalk in the first half but there were still really good opportunities where we didn't get the final pass away when we should be in on goal.
"Early on this season we'd stopped the problem of conceding goals, which was our Achilles heel last season. We've changed that round and became harder to beat - up to this little run of games. Young players are young players, so I'm sure they'll bounce back."
Chesterfield: Parkin (gk), Ofoegbu, Wakefield, Taylor, Smith, Fowler, Hand, Brownell, Rowley, Darwent, Sennet
Substitutes: McKenna, Tippin, Phillips