A goal a minute from time from York striker Richard Brodie punished the Hatters in the first leg of their play-off semi-final.
The Blue Square Premier's leading marksman latched onto a header from Shane Blackett to send a shot nestling into the bottom corner to give the Minstermen a one-goal advantage going into the second leg at Kenilworth Road on Monday.
It was a blow for the Hatters and hard to take considering the amount of chances they created over the 90 minutes.
In fairness both sides were guilty of spurning gilt-edged opportunities on a sodden evening at a packed Bootham Crescent.
The Town dominated the first period with Tom Craddock unnerving the home backline as early as the seventh minute when he guided a shot just past the post following Claude Gnakpa's right-wing cross.
As the Hatters continued to press, playing some lovely football, the hosts had goalkeeper Michael Ingham to thank for keeping the score goalless when he turned Keith Keane's low shot from 22 yards around the post.
That woke York up and Brodie came close to putting them ahead five minutes later when he momentarily broke free in the penalty area. However a fantastic intervention from Blackett blocked the striker's effort as he pulled the trigger.
Another block saved the Hatters on 29 minutes when Adam Newton - playing at right-back instead of the injured Ed Asafu-Adjaye - got in the way of Alex Lawless's shot from 15 yards.
Back came the Town though and as half-time approach three chances went begging to break the deadlock.
Firstly, on 36 minutes, Keane's right-wing corner was flicked on by Blackett to Kevin Gallen who twice in the space of a matter of seconds saw efforts pushed away by Ingham.
Four minutes later the Town came even closer to opening the scoring when Gnakpa hit the post with a shot with the outside of his boot from the edge of the area after getting the wrong side of James Meredith.
Mark Tyler was called into serious action for the first time on the night just four minutes into the second period when leaping to his right to keep out a David McGurk header and two minutes later he saved another header, this time from Brodie.
It was end-to-end and exciting stuff as the Hatters responded to the Minstermen's threat and Gnakpa missed a glorious chance to finally put them in front on 56 minutes when he scooped over Craddock's square pass across the six yard box.
The Town continued to play some confident possession football but Martin Foyle's side sprung into life again on 78 minutes when left-back Matt Carruthers volleyed over at the back-post after Adam Purkiss' right-wing cross had eluded everyone in the penalty area.
Somehow, given all the missed opportunities, it looked as though the game was going to end goalless but then, with the 90 minutes almost up, Brodie reacted quickest to Blackett's misplaced header to race into the box and slot past Tyler to send the home support into raptures.
At half-time, the Minstermen have the lead.
All to play for at Kenilworth Road on Monday.
For minute-by-minute analysis see below.
Live from Bootham Crescent
York City 1 (Brodie 89)
Luton Town 0
FULL TIME YORK CITY 1-0 LUTON TOWN - All the reaction and match action to come. See you at Kenilworth Road on Monday...
90 + 1 min - York sense a second, they are brimming with confidence. We can't afford to give them another one.
90 mins - What a kick in the teeth. We've got four added minutes to find an equaliser.
89 mins GOAL - YORK 1-0 Hatters - Uh-oh, the Town have been punished. Brodie races onto a long ball that eludes the Town defence and BSP's leading goalscorer finishes well past Tyler.
88 mins - The Hatters are trying their best but York are funnelling men back. Howells does well and is fouled down the left but the ref plays an advantage and York clear.
86 mins - Back come the Town as they win their 12th corner of the night, MBH sends a cross that flashes across goal but Gallen, the nearest to it, can't get to it.
85 mins - Pressure from York as they win a succession of corner. Pilks does brillaintly to block a shot from Carruthers on the edge of the area. Great defending.
83 mins - Another chance off target for the Minstermen as Purkiss shoots over from 25 yards that isn't worrying Tyler. Seven minutes left, can either side grab a goal advantage to take to Kenilworth Road on Monday?
79 mins - Smith's on for City and his first action isn't pretty as he sycthes down Murray and goes straight into the book.
78 mins - York spring to life and all of a sudden they spurn a super chance to break the deadlock. Purkiss whips a cross from the right that eludes everyone and finds an unmarked Carruthers at the back stick. However, the left-back can only volley over the bar to the disbelief of the home support. What a let off for the Hatters.
75 mins First change of the evening and it is the Frenchman who is withdrawn. He gets a warm handshake from his manager. He's done well tonight.
72 mins - MBH is primed and ready for action to come. Probably for Gnakpa. We'll wait and see.
71 mins - Claude's down on the far side with a touch of cramp. Money tell looks towards Matthew Barnes-Homer, warming up down the touchline, and implies to "get warm up" to the striker by doing a little jog on the spot.
69 mins - More good possession from the Town as Claude shows terrific skill tight on the far side touchline. The referee gives a foul which draws ironic applause from Richard Money in the visitors' dugout.
67 mins - Chance for York but nothing to worry about as Barrett shoots over the bar from the edge of the area.
64 mins - Sustained pressure from the Hatters with Gallen and Craddock seeing plenty of the ball. We must make this count.
61 mins - It's Bootham Crescent's highest gate of the season: 6,204, including 1,240 from Bedfordshire. Not easy on a Thursday night.
60 mins - All the Hatters now, playing some good stuff and that's encouraging the Town contingent who raise the noise levels behind that goal. Come on Luton! Come on Luton! they cry.
57 mins - Claude quite clearly frustrated by that miss tries his luck from 20 yards that isn't harming Ingham's goal.
56 mins - What a chance...for the Town this time and this time it really should be 1-0. Murray feeds Craddock who beats his marker, drives into the area and squares a left-foot pass across goal for the on-rushing Gallen and Gnakpa at the back-post. They both slide in but it's Claude that connects but somehow spoons the ball over the crossbar from six yards. Unbelievable.
54 mins - Murray is unfortunate to be penalised for a challenge on Brodie and Carruthers is over the ball, on the right-hand edge of the area. Someone remarks "he's got a good left foot." He then contrives to whack it hopelessly high and wide of everyone. Who said that comment? I did...
52 mins - Email from Australia:
"Here in Sydney, Hatters fans had to crawl out of bed at 5am to catch up with the action from you live text. It'll be worth it if we can leave Bootham Crescent without conceding and we'll go off to work even happier if Claude can put the next chance in the back of the net. COYH. SydneyHatters."
51 mins - York have started this half well, shooting towards their noisy fans in the covered terrace. Tyler is called into action to keep out Brodie's back post header. Town living dangerously.
49 mins - First save for Tyler who leaps away to his right to keep out a goal-bound header. Not sure who from to be honest. McGurk was up there. Great deep cross from Carruthers though. Still 0-0. Just.
47 mins - Another chance for the Town - when will they take one? Gnakpa wins a corner down the right that Keane drives in low towards Gallen who hits a firm first-time shot that is straight down Ingham's throat.
46 mins - No changes for either side at the interval. If anything the rain seems to be coming down heavier than it has been.
46 mins And we're off for the second period as the Hatters kick-off attacking the open terrace where the 1,200 fans stand. It's still raining...COYH!
HALF-TIME YORK CITY 0-0 LUTON TOWN - It's been all the Hatters in a very entertaining first half but that's not to say that York have not had chances and looked dangerous themselves. The Town have hit the post&nbsp; through Gnakpa and seen Ingham pull off a great save from Keane's shot. At the other end crucial blocks from Shane Blackett and Adam Newton mean Mark Tyler hasn't had a shot to save. Check back in 15 minutes for all the updates. COYH!
45 + 1 mins - More good work from the Town as Craddock blasts another good chance wide of the post after Gnakpa had done well to lay the ball off on the edge of the area.
45 mins - We've got one added minute at the end of the first half as Craddock does well to go on a slamoning run down the left after good work from Murray but Ingham is well alert to the danger and gathers.
44 mins - Half-chance for the Hatters but it is a half chance. A short corner between Keane and Howells results in the former firing a disappointing low shot wide of the post from the edge of the box.
43 mins - It's all the Town at the minute, one before the break would be truly deserved.
40 mins - Chance as Gnakpa hits the post. Howells does brillaintly to dig the ball out from the left towards Claude who gets ahead of Meredith to guide a shot with the outside of his boot past Ingham but the, unfortunately, the ball comes back off the left-hand post. What a great opportunity.
39 mins - Another dangerous corner from Keane whipped in from the left that falls right onto the head of Gallen but this time the striker heads clean over the crossbar.
38 mins - You do feel that the Town need to take one of these chances while they're on top...
36 mins - Should be 1-0 to the Hatters - tell you about it in a minute...A devious corner from the left from Keane is flicked on by Blackett at the near post, flashing across goal. Gallen, unmarked is first to meet it. His first header is blocked by Ingham before the rebound hits Gallen again who sees his second effort cleared off the line - possibly again by Ingham. How lucky was that?
34 mins - Been&nbsp;a real dearth of chances for the last five minutes and it's pretty even.
29 mins - York coming back into this more and look a threat in the final third when they get it that far. Rankine does well holding the ball up and squares to Lawless who, turns his man before going for goal. It looks all the world that it's going to be 1-0 but another block comes to the Town's rescue...this time it's Newton.
26 mins - Here's the kiss of the death for you...it really is a good game at the minute. The Town are having the better of the ball. Still goalless, though.
23 mins - And then all of sudden it's almost 1-0 to York. Brodie bears down clean through on goal but Blackett comes in with an absolutely terrific sliding block to deny the BSP's top marksmen, when pulling the trigger from 12 yards. Blimey. That was close.
22 mins - The Hatters are playing some good stuff this half, especially in the last 10 minutes.
20 mins - York guilty of making a lot mistakes at the back which allows Howells to feed Craddock. The striker does well, to take a touch away from his marker before hitting a left-foot volley that McGurk bravely blocks behind for a corner.
18 mins - Almost 1-0 to the Town and York have goalkeepr Ingham to thank for&nbsp;a top save. Heslop wins a tackle, the ball falls to Keane 25 yards out. The Town number four hits it first time that looks destined for the top right corner until the keeper sticks out a glove to turn it behind for a corner. What a save.
17 mins - The Town are playing some good stuff. A flowing move, involving Keane, Newton, Craddock, Gallen and Gnakpa results in the Frenchman firing a left-foot shot from just outside the the box that goes wide. Great play. All the Hatters at the minute.
13 mins - More good play from the Hatters forces a corner. Keane whips in dangerously in from the left towards the back-post with Pilkington and Gallen attacking it. They both feel it should be another corner but the lino doesn't agree. Goal kick. Gallen not happy.
12 mins - Another shot on target as the hosts try and up it. Carruthers does well to beat Newton and finds Macklin who shoots high, wide and handsome.
11 mins - Both sides guilty of misplacing passes and slipping over. It's going to be mayhem on this wet, slipperly pitch.
9 mins - A good start from both teams we've I'm being honest but the Hatters have started to pass it well. Encouraging early signs.
7 mins - Chance and a great one for the Town. Gnakpa digs the ball tight in the right-hand corner, passes it to Helsop who whips in a low cross that Craddock gets to first. The striker's neat touch goalwards looks like it's going to creep in but it drifts agonisingly wide of the far post. Unlucky.
6 mins - I don't think he intended that...Gallen wins a free-kick 40 yards from goal that Keane lofts into the box but nobody moved and the ball bounces harmessly wide much to amusement of the home crowd.
5 mins - First shot of the evening as Macklin drags a right-foot shot from the edge of the area wide&nbsp;following a right-wing corner.
3 mins - Plenty of early pressure from the hosts, great atmosphere inside this little, old ground.
2&nbsp;mins - Ooh, another early call from Malone as he books Heslop for a crunching tackle in the middle of the park.
2 mins - Early break for the Town the shape of the returning Gnakpa, bursting into the penalty he goes down under a challenge but refeee Malone isn't interested and the Frenchman incurs the wrath of the home faithful.
1 mins - The rain is still teeming down here as we begin this first of 180 minutes of play-off football.
1 min We're off - at the the second attempt and&nbsp;15 minutes later-&nbsp;as the noise goes up a few decibels, it's the hosts to kick-off, shooting towards the massed ranks of Towns. COYH!
19:58 THIS IS IT
The message is simple: COME ON YOU HATTERS.
19:55 HERE THEY COME
Both sides out on the pitch. Terrific reception. Flags and cards held aloft in the home sections. Plenty of blue, white and orange in the away end. We're almost set.
Great atmosphere inside the ground as anticipating builds. Eight minutes to kick-off now. The Town contingent will have their work cut out to compete with their counterparts this evening. That open terrace does nothing for their noise. Still, they're pretty noisy. Some have come unprepared. Plenty just wearing short-sleeved shirts in the rain.
19:50 MIND GAMES
Andy Hawkins emails:
"The delayed kick-off isn't a Mourinho-esque mind game to get the upper hand? Won't work with Money in charge of the Hatters, hopefully he'll get them fired up. COYH!!!"
19:49 PRESS BOX PREDICTIONS
Andrew Barringer: 0-0. Simon Pitts: "a draw". Mark Wood: "Too nervous to predict". Bill Cole: 1-1. Euan Duncan: 2-2. Ian Pearce: 2-0 Luton.
19:45 FROM NORWAY WITH LOVE
Alexander Nyheim, from Tronheim, emails:
"Big shout from Trondheim, Norway! We will win this game 2-0!"
Its a sell-out in the home ends, you can't swing a cat and a result you can forget any hot pre-match grub. It's all gone!
19:30 KICK-OFF DELAYED
Breaking news: The game has been put back until 8pm. The roads in and around York are absolutely rammed. We'll keep you posted.
19:29 BROLLYS UP
The poor old Town fans are the only supporters open to the element on an uncovered terrace behind the goal to our left as we look in the Main Stand. Plenty are huddles underneath umbrellas or donning the waterproofs. Just over 1,200 are expected to make the journey here this evening. The traffic and weather on the way up was pretty abysmal.
19:25 TEXAS CALLING
Judi Polansky from Ft Worth, Texas, USA, emails:
"I will be reading your text commentary today as it will be afternoon here in Texas and I will be at work. I will try not to yell too much and disturb my co-workers :-)"
19:20 GOOD OMEN?
Ian Gooderham emails:
"Just about to make the short trip to Frankfurt airport where I should get most of your text commentary before my late flight back to Birmingham. So hoping for positive news, the last time I was here and watching your commentary we had a great 2-0 away win in the FA cup. So hopefully a good omen. Come on you hatters from a sunny Frankfurt."
19:14 THE MINSTER-MEN
York: Ingham, Purkiss, Meredith, McGurk, Lawless, Rankine, Brodie, Macklin, Carruthers, Graham.
Substitutes: Parslow, Smith, Gash, Pacquette, Mimms.
19:05 THREE CHANGES
Town boss Richard Money makes three changes to the side that drew at Rushden &amp; Diamonds on Saturday. Ed Asafu-Adjaye, Janos Kovacs and Matthew Barnes-Homer are the ones that don't make it Keith Keane, Claude Gnakpa and Shane Blackett all returning. MBH and Kovacs are on the bench, however, but Ed misses out after picking up a knock in training on Monday.
Hatters: Tyler, Keane, Pilkington, Newton, Craddock, Blackett, Howells, Gnakpa, Gallen, Murray, Heslop.
Substitutes: Kovacs, Hatch, Gore, Hall, Barnes-Homer.
19:00 WET WET WET
We're finally inside Bootham Crescent, there's a buzz inside and outside the ground. And it's teeming it down. The pitch, that had plenty of sand on it last time we were here in February has much, much more grass on it this time around.
16:25 FACEBOOK THOUGHTS
Plenty of positivity and nerves from our fans on our official page. Click here to get involved.
Carl Rowles: 2-0 Luton, Craddock and Howells.
Gray Chapma: 1-0 Luton.
Danny Brown: 5-0 Luton.
Tim O'Donoghue: 2-1 Luton, Howells and Craddock.
David Hird: "Classic Money away performance. 1-0 Luton - Gallen."
Andrew Whitehorn: 2-0 Luton.
Wendy Balzan: "Don't mind as long as we win. Am getting nervous already - COYH!"
Anthony John Allen: 3-0 Luton.
Kyle Brightman: 3-1 Luton.
Petey Staniforth: "We win, Tommy Craddock scores, and Monday becomes the most intense game of the season."
Simog Cog: "I'd like to see us win no matter what the score, COYH."
Craig Penman: 2-1 Luton.
Duncan Sibley: "It will be close - 1-0 Luton - Craddock."
Andy Hawkins: "1-1 tonight, Heslop for us Brodie for York."
Adam Roush: "I'm picking 2-0, risky I know, but I've got a fiver on it."
Mick Nicholson: 1-0 Luton - Gallen.
Jon Bromberg: 3-1 Luton - Craddock hat-trick.
Steve Flood: "1-0 to the Hatters, Keano to bag it. COYH."
Tracy Ring: "3-0. Please win! COYH."
Andy Brett: "6-0, let's destroy them. COYH."
16:10 WET WET WET
Travelling North we wonder where the sunshine that has blessed us over the past week or so as gone as miserable rain pours from the sky. Its expected in York too, so the pitch at Bootham Crescent really could make of an interesting 90 minutes of football.
15:00 LIFE IS A ROLLERCOASTER
The Hatters' first ever campaign in the Blue Square Premier has had, as Gary Sweet said in his programme notes against Altrincham a few weeks back, "more rollercoasters than Alton Towers".
Well we've got some news for you: over the course of the next week expect more twists and turns than Nemesis and get ready to feel the kind of nerves that somersault inside your stomach when you're in a queue...at Alton Towers.
But that's what the Play-Offs do to you and I fully expect nervous excitement to be flowing through the bodies of the Town fans waiting to get inside Bootham Crescent this evening for the first leg against the Minstermen.
And while we're quoting senior members of the Luton Town hierarchy, remember Richard Money's "messy pants" remark as the Hatters began to rack up a succession of goal-filled victories?
Well, put that phrase together with the "Play-Offs" and you could be a marketing manager's dream at Pampers!
But forget all this talk of nerves. Afterall, what have we got to be nervous about?
Riding the crest of a wave, the Town are on the march, unbeaten in their last 14 matches, winning 10, scoring a phenomoal&nbsp; 42 goals in the process.
Add the fact that goalkeeper Mark Tyler and his defence have conceded just 10 goals in the same period, keeping seven clean sheets and then you can see why the Hatters squad are brimming with confidence going into what many call the "end of season lottery".
First legs of Play-Off Semi-Finals are usually incredibly cagey affairs so you can better your bottom dollar than it'll probably end up 3-3 tonight.
But after all that's said and done this evening it will only be half-time and both teams will be at Kenilworth Road on Monday for the second leg.
Hold on to your hats...it's going to be one helluva ride...
Well, whatever happens at Bootham Crescent this evening your official website will have everything covered: every step of the way.
If you can't make the match then we'll have all the goals and incidents as it happens live with the usual news in the run-up to kick-off with team line-ups and plenty of chat as your official website has, as ever, the usual updates keeping you bang up-to-date with all the action - and in a number of ways.
There's none of those boring ball-by-ball "defensive thrown-in taken by Luton left-back" updates as we continue to try and bring you an updated and detailed text commentary. This is a great way to keep in touch and has been popular to those supporters not able to get to a computer or a radio as the service is also available and is updated live on our WAP site.
On Hatters Player you all have access to our live commentary. Remember, Player is available as ever which means you all have access to our live commentary. If you haven't heard it yet then where you have been? It's brought to you by Simon "Statto" Pitts - who is quickly making a name for himself with commentary that is the envy of all the competition. His commentary in injury time against Oxford has made international radio while groups in his honour have sprouted up on social networking site Facebook. He's here at Bootham Crescent and ready for the Play-Offs!
Afterwards we'll have all the reaction from the men that matter this after, bringing you exclusive video content!
As always we'll have plenty of content to keep you interested as we'll have all of the post-match reaction as well as match action from Gareth Owen to follow after the final whistle. Be sure to check out www.hatterspics.co.uk - our brand new online image library.
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Enjoy the game.