Old boy David Ferguson scored the only goal of the game as Boston United were sunk by York City - in a game blighted by three late red cards.
The former Pilgrims loanee slotted home a 73rd-minute winner before climbing the fence to celebrate with his fans.
But the final 10 minutes saw Boston’s Andi Thanoj and Ben Middleton receive straight red cards and City’s Simon Heslop also dismissed.
An after a three-week wait for a return to action, the team in amber didn’t really get going against a side who deserved their victory following an improved second half.
The Pilgrims lined up without ex-York striker Reece Thompson, finally serving his one-match suspension for the red card picked up against Leamington three weeks earlier.
However, Ryan Qualter and Middleton, back on loan from Harrogate, were named in the United squad to face their former club.
Jake Beesley was handed a debut in attack, named up front with Jack Dyche, whose loan spell from Scunthorpe United ended with his first start for the Pilgrims.
Jonathan Wafula also made his debut from the bench.
The forgettable first half offered little goalmouth action with both sides looking rusty, neither helped by a boggy pitch which began to cut up early on.
Passes were stuck in the mud or overhit to compensate and neither side could find their rhythm.
The Minstermen’s Louis Almond forced a near-post save from Jon Stewart before the offside flag was raised, while Beesley’s tame header gave City keeper Adam Bartlett a heart-in-mouth moment as it skipped swiftly off the mud before being gathered.
The team talks did the job as the tempo was instantly raised in the second half.
York, laboured and clunky in the first half, suddenly had the look of a top-five side.
Almond’s drive on the turn was blocked and a second effort was deflected wide byJordan Keane.
Stewart then got down well to squeeze Adriano Moke’s drive wide of this upright and repeat his trick when Almond smashed the ball his way.
Boston were having to defend deep, but a rare foray forward saw Thanoj force Bartlett into a low save from his half volley.
That appeared to add some spark to the United attack, Thanoj firing a hopeful effort over before Bartlett reacted well to tip away Benny Igiehon’s snapshot and Ashley Hemmings’ tame header.
Ferguson put the Minstermen in front in the 73rd minute, afforded too much space on the left-hand side of the Boston box before slotting a low drive beyond the onrushing Stewart, who had frustrated the home fans with his less-than-speedy attempts to keep play going.
There was still time for three lare red cards, York’s Heslop receiving a second yellow for a late foul on Thanoj, and the Boston man seeing a straight red for a reaction where he grabbed his opponent in a brief headlock during the ensuing melee.
Seconds later and Middleton was dismissed for a lunge at Raul Correia, the Pilgrims now seeing two players facing three-match bans in a day to forget.
YORK: Bartlett, Parslow, Ferguson, Bencherif, Newton, Moke (Smith 64), Pattison, Heslop, Kempster (Correia (66), Almond (Almond 86), Connolly. Subs (not used): Brown, Simpson.
UNITED: Stewart, Middleton, Keane, Qualter, Brogan, Rollins (Wafula 78), Thanoj, Abbott, Hemmings, Dyche (Igiehon 59), Beesley (Tshimanga 78); Subs (not used): Atkinson, Willis.
Ref: John Matthews.
Att: 2,461 (246).