The Spireites youth team endured a nervy time in overcoming Stourbirdge with a last-minute winner in a 3-2 away win in the first round proper of the FA Youth Cup.
George Milner opened the scoring for Chesterfield with his tenth goal of the season, but with 12 minutes to go the visitors were 2-1 behind and it took two late goals from substitute Curtis Morrison to see Chesterfield just about through.
The win takes the Spireites into the second round where they will meet Sheffield United at home.
Academy manager Mark Smith wasn't totally satisfied with the performance but was happy to be through to the next round.
He said: "It took us until about 70 minutes, at which point we were 2-1 down, until we got playing and we finally ran their legs out of them.
"They had a right go at us for 70 minutes and caused us problems by getting in our faces and running at us. Then in the last 20 minutes we started to create a few chances and Curtis popped up to put us through.
"It was a bit of a gamble using him as he's only had a few days training but we he went on and got on the end of two balls in the box, which was good.
"We're into the next round, that was the main thing. The next game is the big one for us and the objective for us was to get through, and we did."
The second round date with the Blades is scheduled for the week of November 21, with a confirmed date a kick-off time to be announced in due course.
"We're really pleased with the draw," said Smith. "We tend to do better against the category one and two teams and with Sheffield United being category two they're likely to give us a bit more time on the ball and that's when we could hurt them."
Chesterfield team: Parkin (gk) - Hudson, Randle, Holmes, Smith, Greaves, Marshall, Rowley, German, Milner, Daswell
Subs not used: Jarrald, Morrison, Brownell