Nine-man Chester slipped to defeat away at Port Vale after a crazy second-half performance at Vale Park.
Ritchie Partridge hit the bar for the visitors before Danny Glover slid in an opener for the hosts after the break.
Then Chester had Laurence Wilson sent off for a reckless tackle on Steve Thompson, before Glenn Rule was dismissed for a second yellow card.
Rob Taylor struck from point-blank range to double Vale's lead and James Lawrie curled home to wrap up the win.
Wilson's red card came on his return to the City team after a one-game ban for running up five bookings.
He now appears set for an automatic three-game suspension.
Rule looks set to serve a two-game ban after running up his second red card in only his fifth league start of the campaign.
But right-back James Vaughan, who was completing a two-game ban at Vale Park, is now available for Saturday's home game with Gillingham.
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Booked: Howland.
Goals: Glover 59, Taylor 73, Lawrie 89.
Sent Off: Wilson (71), Rule (72).
Booked: Rule, Roberts, Barry, Dinning.
Att: 4,448.
Ref: Andy Hall (W Midlands).
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