Match ends, Macclesfield Town 3, Chester FC 1.
Waide Fairhurst scored the goal of a lifetime as Macclesfield brought FA Cup heroes Chester back down to earth.
After giving Macc the lead against the run of play with a controversial 39th-minute penalty, Fairhurst added a second as he smashed in a stunning right-foot 35-yard screamer.
Matthew Barnes-Homer added a third shortly after the break.
Ben Heneghan pulled one back with a close-range header, but Chester rued Sean McConville's missed penalty.
The spot-kick was saved by Rhys Taylor - after McConville had been felled by Liam Hogan - and it proved crucial, as was a disallowed Kieran Charnock header and John Rooney hitting the post, all when the score was still 0-0.
The visitors were forced to turn out in Macc's turquoise away shirts because of an unfortunate colour clash.
Chester, exuberant after their weekend FA Cup first-round win at Southend, were comfortably in control for most of the first half, repeatedly going close.
Centre-halves Matty Brown and Kieran Charnock had headers cleared off the line and Craig Mahon's low 25-yard shot was well kept out by home keeper Rhys Taylor, who made a string of saves.
But the award of Macc's late first-half penalty following Jamie Menagh's challenge on Paul Turnbull transformed the contest.
Chester manager Steve Burr told BBC Radio Merseyside:
"I've never been involved in a game of football quite like that, where any team of mine have played so well and lost.
"I was flabbergasted at half-time when we went in 2-0 down as I didn't really know what to say to the lads.
"But it's about putting the ball in the back of the net. And, although I'm full of pride for the way we played, we didn't take our chances.
"Their penalty was completely against the run of play and then the lad hits an unbelievable strike.
"You could have had had three keepers in and they wouldn't have saved that. It was their night and good luck to them."
- 2HallsBooked at 87mins
- 6TurnbullBooked at 56mins
- 10FairhurstSubstituted forMokeat 86'minutes
- 14MenaghSubstituted forTourayat 65'minutes
- 16McConvilleBooked at 72minsSubstituted forO'Keefeat 76'minutes
- 19HobsonSubstituted forOatesat 65'minutes
- Darren England
- Shots on Target
Second Half ends, Macclesfield Town 3, Chester FC 1.
Attempt missed. Matthew Barnes-Homer (Macclesfield Town) left footed shot from the left side of the box misses to the left.
Foul by Josh O'Keefe (Chester FC).
Liam Hogan (Macclesfield Town) wins a free kick.
Attempt missed. Arthur Gnahoua (Macclesfield Town) left footed shot from outside the box is too high.
Andy Halls (Macclesfield Town) is shown the yellow card.
Substitution, Macclesfield Town. Adriano Moke replaces Waide Fairhurst.
Attempt missed. John Rooney (Chester FC) right footed shot from outside the box misses to the left.
Substitution, Chester FC. Josh O'Keefe replaces Sean McConville.
Attempt missed. Chris Holroyd (Macclesfield Town) header from the left side of the box misses to the right.
Sean McConville (Chester FC) is shown the yellow card for a bad foul.
Foul by Sean McConville (Chester FC).
Scott Barrow (Macclesfield Town) wins a free kick.
Attempt saved. Rhys Oates (Chester FC) right footed shot from outside the box is saved.
Attempt missed. Matty Brown (Chester FC) right footed shot from the right side of the box misses to the left.
Substitution, Chester FC. Ibou Touray replaces Jamie Menagh.
Substitution, Chester FC. Rhys Oates replaces Craig Hobson.
Corner, Chester FC.
Attempt saved. Kingsley James (Chester FC) right footed shot from outside the box is saved.