IT was the biggest week of the Blues' season so far - and it ended in double heartbreak.
Two brave, single-goal defeats were all Mark Wright's men could manage from clashes with Wrexham and fallen giants Leeds United.
Having lost 2-1 to their cross-border visitors in League Two on Sunday, Chester turned in a battling display at Elland Road just two days later in round one of the Carling Cup.
Eirik Bakke's fortuitous second-half strike won it for the Championship side - but boss Wright was happy with his play-ers' gutsy display.
'There were a lot of good performances from us and we acquitted ourselves well,' he said. 'Overall, I thought we could have got something out of it. I'm pleased with what they did and I'm proud of what they did.
'They've had a bit of a talking to since the Wrexham game and, on another day, we might have snook something.'
Blues striker Gregg Blundell squandered a great chance to level in the 72nd minute and Wright added: 'Gregg maybe should have done better. It looked like a shot to me but he said he passed. It was only a couple of feet away.'
Leeds assistant boss John Carver described the result as 'a massive relief '.
'The performance wasn't great but it's a win,' said Carver. 'Let's give Chester a bit of respect - they came out, they got at us and they put their foot in. Obviously, Wrighty had a word with them and they got among us and unsettled us.'
Blues centre-back Ashley West-wood was more happy with how the team defended at Elland Road after giving away sloppy goals in recent defeats to Hereford and Wrexham.
He said: 'We've got to take something out of the game. Our keeper has not had much to do and Leeds are a top Championship team.
'We definitely held our own and put a good show on.
'The goal was obviously un-lucky on our behalf. It's ricocheted like a pinball, hit the post twice and ended up in the back of the net.'
On Sunday, Wright laid the blame for his side's 2-1 loss squarely at the feet of referee Uriah Rennie, who failed to send off Wrexham goalkeeper Mike Ingham for handling outside his penalty area.
Chester's Ricky Ravenhill saw red for a foul on the Dragons keeper and visiting centre-back Steve Evans was dismissed late on.
Wright said: 'The reality is - and I've seen it on the video so I know what I'm talking about - the keeper is a yard and a half outside his box.
'I can't condone Ricky going for the ball like he did. Even though he didn't make any sort of contact whatsoever, he's put his foot through.
'But it's a goalscoring opportunity and their goalkeeper should be sent off. They've got it way wrong.'