Haydn Hollis headed Town’s equaliser from a corner with 15 minutes to go to cancel out Scott Garner’s opener in blustery conditions at the Jakemans Community Stadium.
Young goalkeeper, Dylan Wharton, 18, was the hero in the penalty shootout, saving from former Spireite Jordan Burrows and then another ex player, Connor Dimaio, fired wide, as the Blues won 4-1.
Here are Liam Norcliffe’s player ratings from the game...
1. Dylan Wharton 6
A rollercoaster of a night for the 18-year-old in difficult conditions on his Chesterfield debut. He only found out he was starting on the coach journey down. He was at fault for Boston's opener as he got caught underneath the ball from a corner. He was almost left red-faced when opposition goalkeeper Ross Fitzsimons hit the crossbar with a goal-kick that got caught in the wind, and there were a few other nervy moments. But he proved to be the hero of the night when he saved Jordan Burrows' spot-kick in the shootout, gaining him an extra mark from me. A night he will never forget. Photo: Phil Tooley
2. Josef Yarney 5
The right wing-back was lucky not be sent off after kicking the ball away in the second half when he was already on a yellow. His powerful goal-bound shot was blocked by Boston defender Joe Leesley for a corner, which Town scored from with 15 minutes to go. Had another effort in the first half which he blazed over. Photo: Phil Tooley
3. Will Evans 6
The centre-half didn't do a lot wrong. Possibly a little bit lucky not to give a penalty away in the first half when Boston's Rollins hit the deck. Cleared one away close to the line with Wharton out of goal. Had a half-chance at the far post in the second half but he side-footed Maguire's cross wide. Photo: Phil Tooley
4. Haydn Hollis 6
Like Wharton, a rollercoaster of a night. Rowe wants Town to bring the ball out from the back more and Hollis was asked to do a lot of that. He did a lot of good things, but he almost cost them a few times as well. But that's understandable because Rowe is asking them to do things they are not used to. He redeemed himself with a lovely flicked header at the near post which nestled in the far corner, bumping him up a mark to a six. Photo: Phil Tooley