Silkmen through to play-off semis as last-gasp goal seals 2-1 derby win over Chester
By Oliver Evans 29th Apr 2026
Macclesfield are through to the National League North play-off semi-finals thanks to a 98th minute winner from Luke Duffy.
Macc dominated throughout the game and were rewarded very late on to beat their bitter rivals.
The Silkmen had the first chance of the affair, when Paul Dawson's through ball found Duffy, who twisted and turned but his shot was well saved by the feet of Bobby Jones in the Chester goal.
Macclesfield would dominate the opening ten minutes, with Isaac Buckey-Ricketts going close from an Elliot Osbourne free-kick and James Edmondson clipping the outside of the post from a Luis Lacey cross.
The Macc pressure continued to mount, as Edmondson and Lacey linked up again, but the midfielder's shot was easily saved by Jones.
Despite the half hour of Macclesfield pressure, Chester would open the scoring with their first shot on target of the game, as Mottley-Henry found Connor Woods on the right-hand side of the box who fired below Rogan Ravenhill and into the back of the net.
A minute after Macclesfield fired back, as another great Luis Lacey cross found the hands of Bobby Jones via a Duffy volley.
The half time whistle blew with the Silkmen having to rue their missed chances.
Macclesfield started the brighter in the second half once again, with Buckley-Ricketts curling a shot just wide of the post the best chance of the opening ten minutes.
The Silkmen finally broke their deadlock after 66 minutes when Dawson found Luke Matheson in space on the right, who fired a low cross into the feet of makeshift centre forward Josh Kay who hit it into the roof of the net from close range.
Kay was back in the box ten minutes later, setting up Edmondson for a powerful volley that was easily caught by the Chester 'keeper.
Then, with ten minutes to play, Cameron Borthwick-Jackson found space on the edge of the area and rifled a shot off the crossbar, which was then followed up by another Edmondson volley, this time going over the bar.
Into additional time Macclesfield continued to dominate, with Dawson hitting a shot from the edge of the box just over the bar.
And then, with mere seconds to play, into the 98th minute, Duffy sent a corner into the box that couldn't be kept out by the Chester 'keeper.
Macclesfield travel to Kidderminster on Saturday, May 2, for the semi-final.
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