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Gillingham were knocked out of the FA Youth Cup on penalties by Charlton Athletic.
Tuesday night's match finished 1-1 after extra-time and eventually went into sudden death penalties which Charlton won 9-8.
Chatham Town hosted the second round match after the Gills had eased past Leatherhead in the opening round at Priestfield with a 7-1 win.
The Gills, managed by former player Craig Stone, were the underdogs against Charlton, a category two academy, but took the lead midway through the opening half.
Josh Chambers scored the opener, firing home from 20 yards.
Gills keeper Charlie Walker saved well from Tyreece Campbell and towards the end of the half was also called upon to deny Jeremy Santos.
Charlton’s England youth international keeper James Beadle kept out a free-kick from Bailey Akehurst.
Beadle saved well in the second half to keep out an effort from Harry Maher but the visitors levelled on 62 minutes as Dylan Gavin headed home from a corner.
Campbell wasted a good chance to win it for Charlton in the final minute of normal time, meaning an extra half hour of football.
Neither side managed to find the net in extra time and the match went to penalties. It took 20 penalty kicks to decide the winner.
Walker saved from Santos with the first of Charlton’s efforts and Gerald Sithole struck for Gills to give them the early advantage. But Mack Reilly got Charlton off the mark and when Matt Baker failed to convert it was all-square.
The next 14 penalties were all converted. Gills’ seven were scored by Maher, Akehurst, Chambers, Ethan Smith, Ronny Nelson, Vinnie Medhurst and Harvey Linott. With the shootout in sudden death, Joseph Grode’s effort was saved and that gave the Addicks victory.
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