It was a first ever defeat against Braintree for York, having never lost in their previous six meetings, as a second-half strike from substitute Jermaine Francis proving to be the difference.
Braintree had led in the first-half when experienced striker John Akinde had found a route through on goal, before calmly dispatching past Harrison Male.
York had waited just ten minutes before drawing level, with Josh Stones powering home his sixth goal in a City shirt from inside the area.
But Braintree ensured the points remained in Essex after substitute Francis came on the field and bundled Kyreece Lisbie’s cross over the line.
The defeat means that the Minstermen remain 11 points adrift of Barnet, who will play at 5.30pm against Altrincham, whilst Forest Green Rovers also lost in a 3-0 hammering at AFC Fylde.
Oldham Athletic have been the only team in the top six to not lose, beating fifth-placed FC Halifax Town, and narrowing that gap to York to eight points.
Braintree came into this match in good form, having lose just one of their last seven matches in the National League.
That has seen Steve Pitt’s side pull away from the relegation zone, with nine points now separating the Iron and Fylde in the bottom four.
A midweek 3-1 win against Gateshead, despite being behind at half-time, was attended by the City management team, with Adam Hinshelwood declaring it was the best Braintree team he had ever seen.
That’s been aided by the performances of Kyrell Lisbie on the wing, along with his twin brother Kyreece, whilst experienced striker Akinde leads the line for the Essex-based club.
Hinshelwood looked to counter this with two changes from the York side that celebrated a 1-0 win away to Yeovil Town last Saturday, with Adam Crookes being awarded a first start since November.
Tyrese Sinclair was also put back into the starting 11, replacing Lewis Richardson who dropped to the bench.
Cam John was the other absentee, having struggled with a slight hernia problem this week.
Braintree had impressed so much in their midweek win that Pitt opted to make no changes to the team, naming an unchanged side from that win at Gateshead.
The only difference for the Iron was the recall of winger Jermaine Francis, who returned to the bench after international duty with Grenada.
Hinshelwood had been hugely complimentary of York’s opponents, and with their recent form, it will have been key that his side didn’t fall to an early disadvantage.
They came close as Chay Cooper weaved his way into space inside the area, but was thwarted by the glove of Harrison Male.
Tyrese Sinclair went close when beating Jacob Pinnington on the byline, but his curling effort was held by Henry Gray.
Marley Marshall-Miranda was next to go close, after drifting into space 25-yards from goal, and bending a venomous attempt narrowly wide of target.
With 25 minutes played, the City net bulged as Braintree took an admittedly deserved lead in Essex.
After dispossessing a defender, Akinde broke through one-on-one with Male and showed his composure, producing a side-footed effort into the bottom right corner.
York needed a response after Dan Batty had a long-range strike blocked, but it would lead to the corner which would draw the Minstermen level.
After Batty’s corner was failed to be dealt with by the Braintree defence, it fell kindly to Stones, who showed prowess with an instinctive low finish past Gray.
It would be the last action of the half for York, who were quick in their start to the second-half.
Sinclair then latched onto a crossed ball from the right and scuffed a strike at goal, which was impressively cleared off of the line by Aidan Francis-Clarke.
Male was again called into action with Braintree growing back into the game, parrying Matt Robinson’s header away from goal.
Braintree should have gone ahead when Kyreece Lisbie worked his way into the area and had the goal at his mercy – but somehow missed the target from nine yards out.
Hinshelwood looked to his bench to change York’s fortunes, introducing Lenell John-Lewis and shifting Stones wide.
But it was the change for Braintree, with Francis now on the pitch, that would prove fruitful.
The winger made an instant impact when putting the Iron back in front, bundling Kyreece Lisbie’s flick towards goal past Male, making it 2-1.
City again needed a route back into the match, and were left feeling more and more frustrated when Callum Howe rose highest for Batty’s cross, only to miss the target from within the area.
That needed equaliser would never come, with York taking a blow in their push for the title as that gap to reach Barnet threatens to reach 14 points.
BRAINTREE TOWN: GRAY, PINNINGTON, FRANCIS-CLARKE, LANGSTON, CLAMPIN, MARSHALL-MIRANDA, ROBINSON, KYREECE LISBIE (OKONUWU, 89), COOPER (BLACKWELL, 67), KYRELL LISBIE (FRANCIS, 60), AKINDE
SUBS NOT USED: HAXTHAUSEN-NIELSEN, JUDGE
GOALS: AKINDE (25), FRANCIS (66)
YELLOW CARDS: PINNINGTON (18)
YORK CITY: MALE 6, FELIX 6, FAGAN-WALCOTT 6, HOWE 7, CROOKES 6 (FALLOWFIELD 6, 60), BATTY 6 (AGUIAR, 84), HUNT 6 (CHADWICK, 84), PEARCE 6, LUAMBA 6 (JOHN-LEWIS 6, 60), STONES 7, SINCLAIR 6 (NATHANIEL-GEORGE 6, 73)
SUBS NOT USED: WATSON, RICHARDSON
GOALS: STONES (35)
YELLOW CARDS: MALE (83)
YORK’S STAR MAN: CALLUM HOWE. Dealt with the threat of Akinde for parts of the game and won a lot in the air.
REFEREE: CALLUM WALCHESTER
ATTENDANCE: 1,137 (371)
SHOTS (ON TARGET): 9 (4) | 5 (3)
CORNERS: 7 | 4
OFFSIDES: 2 | 3
FOULS: 8 | 12
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