Stevenage boss Mark Stimson returned to his former club for the first time and left with all three points, plunging Grays into the Nationwide Conference relegation zone.
Stimson's new outfit barely deserved the three points but for the umpteenth game in succession, Blues squandered chance after chance while their opponents were aided by the fickle hand of luck.
The visitors' first goal was heading straight into the arms of Ashley Bayes when it took a deflection off Dean Howell and found the top corner.
Foolishly Andy Sambrook was then sent off for two fouls on another ex-Blue, Mitchell Cole, in a mad 60 seconds just before the interval leaving his side with a mountain to climb.
Grays' current boss Justin Edinburgh hit out at referee Gary Lewis for the sending off, claiming the first card was not a booking.
It probably wasn't but, Edinburgh can't have missed the two or three times Sambrook clattered into Mitchell Cole prior to his first yellow.
But you can sympathise with Edinburgh's rage. Most of the key decisions in games are going against his side at the moment and it is impossible not to agree with him when he says luck has deserted his team.
"I know I sound like a broken record," Edinburgh said. "But we are not getting that rub of the green at the moment. Nothing is going for us.
"We have dominated possession again and we are creating chances but we just can't take any of them. You can't coach that. You can't coach people in pressure situations to put the ball in the back of the net.
"I can't be critical of the players, they gave everything. If we weren't creating chances I would be worried but we are, we are just not putting them away."
On Sambrook's sending off, Edinburgh added: "The second booking OK, but the first tackle was not a yellow card."
Stimson's view differed somewhat: "Sambrook took Cole out three or four times before the booking and maybe if the referee had stopped it earlier he might not have been sent off."
But the Boro boss does admit to some sadness at his former side's plight.
He said: ""It does sadden me to see where Grays are now," he said. "I had some fantastic times here and I don't want to see them at the bottom of the league. I want to see them up there challenging for things with us.
"But I'm sure they will get out of this. They have got some good players and they will be alright."
Stimson would not have needed to do too much homework on his former charges, six of whom he brought to the club.
But the appearance of one of those may just have thrown him a bit.
Leroy Griffiths left the Blues under a cloud just days before the club's first FA Trophy triumph in 2005 amid rumours of a bust-up with a team mate on a training trip to Spain.
Stimson's decision to ostracise the fans' favourite was one of the few decisions during his tenure at the Grays that was met with opposition by Blues supporters.
Those fans have been calling for Griffiths' return ever since and they got their wish on the eve of yesterday's clash when Edinburgh raided his former club Fisher Athletic to bring him back on loan.
Griffiths renewed his near telepathic understanding with Dennis Oli and should have wounded his former boss with an early goal.
Twice he went close to netting in the opening exchanges with Stevenage's Barry Fuller handing him his first chance on a plate.
The full back sold his keeper Alan Julian short with a header which Griffiths latched on to. But he could only scuff his shot goalwards allowing Julian to clear with his legs.
He then fired straight at the Stevenage stopper after a give and go Oli, who then headed straight at Julian, as Grays made the early running.
It wasn't just Stimson retuning to the New Rec though as Boro included both John Nutter and Cole in the starting line-up and that pair combined to create Stevenage's first chance, Nutter dragging a shot wide from the edge of the box.
Boro then got the decisive opening goal when Fuller's crisp volley from the edge of the box took a wicked deflection off Dean Howell which took it past Ashley Bayes.
Jamie Stuart then made a fantastic goal-line clearance to prevent Cole from scoring on his first return to Grays after Jon Nurse had put Blues on the back foot.
Things went from bad to worse on the stroke of half time when Sambrook collected two bookings in the space of 60 seconds to leave his side with 10 men.
His first booking, a tug on Cole's shirt as he broke from his own half, was dubious but when added to the numerous earlier fouls on the ex-Southend man, probably deserved.
The second was just pure madness, scything down the same opponent on the touchline, leaving referee Gary Lewis with little alternative.
Cole continued to torment Grays after the re-start, dragging a shot just wide when well placed.
Stuart then made his second goal-saving intervention of the day to deny Santos Gaia after Bayes had spilled Daryl McMahon's free kick.
Edinburgh threw on Cameron Mawer and Aaron O'Connor and switched to his 3-4-2 formation and the changes nearly paid off when O'Connor swivelled and smashed the ball against the underside of the bar. The ball came out to Howell who should have scored but rippled the side netting instead.
Boro countered and doubled their advantage after a rapier-like counter attack. Nurse sped down the right as the Blues defence parted before squaring the ball to Steve Morison who tucked the ball past Bayes.
Stevenage's top scorer then went close with two headers, the first inches over the bar and the second thwarted by Bayes with Cole hacking the rebound over.
Plucky Grays showed that spirit is not a problem though by continuing to press despite their numerical disadvantage and O'Connor was denied only by a last-ditch tackle by Nutter.
O'Connor went close again in the closing stages when he skipped past Gaia only to fire straight at Julian.
A consolation goal was the least Grays deserved.
By Ryan Goad
Thanks to the Thurrock Gazette for the match report.