Alan Devonshire made two changes to his side for the trip to the champions, as Shawn McCoulsky and Remy Clerima dropped out of the lineup, as Ashley Nathaniel-George and Tristan Abrahams replaced them. 
The hosts had the first chance to open the scoring, as Miguel Freckleton drove down the wing, passed back to the edge of the box to Tom Naylor who fired over the crossbar. 
Tristan Abrahams had a chance of his own minutes later, picking up the ball on the halfway line, dribbling into the box and past Tyrone Williams, but his effort rolled into the hands of Harry Tyrer. 
Just after the 20 minute mark, Maidenhead had another great chance to take the lead. Abrahams won the ball back inside the Chesterfield penalty area and found Nathaniel-George running into the box, but the winger's strike deflected behind for a corner. 
The Magpies kept pushing for the opener, and 5 minutes later another opportunity presented itself when Nathaniel-George’s ball into the box found Reece Smith whose volley flew over the Spireites goal. 
On the half hour mark, Chesterfield took the lead despite Maidenhead's pressure. Armando Dobra picked up the ball on the byline and slid it across goal for Liam Mandeville to tap into an empty net. 
The Spireites doubled their advantage not long after in almost identical fashion. Dobra played another ball across goal, with Joe Quigley the man to tap home this time for the champions. 
HALF-TIME - Chesterfield FC 2 - 0 Maidenhead United 
Maidenhead started the half brightly, as they looked to get on the scoresheet, and almost did though Tristan Abrahams. The striker received the ball, spun past Williams but his shot sailed over the crossbar. 
Abrahams would get on the scoresheet a few minutes later, as Reece Smith’s shot deflected into the path of the striker who tapped home from just inside the six yard box to half the deficit. 
Not even 5 minutes later, the Magpies drew level. Sam Barratt’s free kick was headed up into the air, and Kevin Lokko rose highest to poke the ball past Tyrer and into the back of the net. 
Chesterfield had a great chance to retake their lead as a ball was floated to Quigley, whose header looked destined for the back of the net, but Craig Ross was across goal quickly to keep it out. 
The hosts thought they took the lead with 20 minutes left, as after some good linkup in the box, the ball found its way to Armando Dobra in the box, but his shot bounced back off the post before being cleared away. 
With minutes left of the game, Chesterfield would eventually retake the lead. Ollie Banks found himself in space some distance from goal, and fired a shot which found its way into the bottom left corner. 
FULL TIME - Chesterfield FC 3 - 2 Maidenhead United 
Chesterfield FC - Harry Tyrer, Tom Naylor, Jamie Grimes, Liam Mandeville, Darren Oldaker, Michael Jacobs, Tyrone Williams, Miguel Freckleton, Armando Dobra (Banks 75’), Jeff King (Clements 70’), Joe Quigley 
Maidenhead United - Craig Ross, Zico Asare, Sam Beckwith, Will De Havilland, Kevin Lokko, Ashley Nathaniel-George (Adams 65’), Jayden Mitchell-Lawson (Massey 77’), Casey Pettit, Reece Smith, Tristan Abrahams, Sam Barratt (Sho-Silva 84’) 
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