It's knocking on for 12 years since these two sides last met, with the Hatters having tumbled from League One to the Blue Square Premier across two tough seasons in 2009/10 and then 2010/11.
Manager Paul Simpson was without Ryan Edmondson, who served the first of his three-game suspension, and Paul Huntington missed out as a precautionary measure with a slight thigh niggle.
That brought Morgan Feeney into the heart of the defence with Jayden Harris starting in a midfield berth. Duncan Idehen and Jack Stretton were drafted onto the bench.
Stockport started brightly and a run from Hippolyte was spotted by Collar. He drilled hard but Feeney was across to make a fantastic block.
The corner was initially met by Feeney, but his clearing header was guided back into the mix by Horsfall. Hippolyte connected with an acrobatic 12-yard scissor kick but it whipped just over the bar.
Moxon, wearing a protective headband over the three stitches he picked up on Saturday, stuck close to Guy as the pair broke up a spell of home possession. Whelan stayed wide, and his ball over the top skipped off the surface and behind the goals as Gibson tried to chase it down.
Holy watched a raking free kick from tight by the left touchline from Brown zip past his upright as Madden and Horsfall both tried to get a touch.
But it was United's turn to have a corner when Gibson showed strength and trickery as he faced two blue shirts. Guy delivered, and Whelan was disappointed as he sent his 10-yard nod high into the stand.
Both teams pressed high, and Madden found himself with time in the box when a corner from MacDonald dropped from high. He touched it then shot low but the block was made.
It was a break from nowhere that caught Carlisle flat-footed when a contest from a throw saw Madden pull wide. He turned quickly and popped a pass over the top, and Hippolyte's pace took him clean through as he broke out of his own sector. With just Holy to beat he calmly slotted it into the net.
Holy produced a top class save moments later when Hussey overlapped on the left flank. Collar hit the afterburners to meet the delivery and his point blank header had goal written all over it until the big stopper spread himself to beat it away.
Collar had to be stopped again when he controlled well after Croasdale had fed it onwards. He got the shot away but Feeney and Whelan shut him down.
Mellish was pushed forward into midfield, with Armer and Back dropping deeper to make it a back four as the away team looked to make their presence known.
That nearly came on 40 minutes when Armer sent the ball long from the edge of his own box. Gibson was after it but Hinchliffe sprinted off his line to make the clearance into the stands.
Another trademark free kick from MacDonald with his left boot, from out wide, brought a heart in mouth moment just before the break. Three attackers tried to get a touch and Holy was mightily relieved as it skipped past him and his post.
A neat trap and cheeky backheel from Gibson deserved better as he put Armer free and clear on the left flank. The cross was too high for both Dennis and Harris.
Fit again Jack Stretton was on for Harris at the start of the second half, and he was in action immediately as he let a throw from Armer ghost past his chest. He tried to lift it over Brown, who appeared to stop it with his hand. The referee showed no interest in the loud appeals.
Moxon intercepted to spark a surge forward from deep inside his own half, and he skipped past two challenges with Dennis and Gibson in support. He opted to let one fly but he couldn't keep it down.
United were a whisker away after a composed build-up on 53 minutes. Moxon and Armer used the space on the left, and Armer popped it inside to Stretton on the 18-yard line when his delivery was charged down. A shot was blocked, but Gibson was on hand to thunder it through bodies. It wasn't too far away.
Whelan was unmarked when the corner was sent in, but he had to readjust and his header went astray. The keeper kicked long and Madden was onto it in a flash. He tried an ambitious volley on the spin but that was also wayward.
The away revival was nipped in the bud as Madden and Collar linked to carve a path. The cross begged to be put away and Kyle Wootton jumped to power a header into the top corner.
A foul on Mellish gave Moxon a chance to try his luck from 28-yards, dead central, but he was disappointed with himself as it started high and wide and stayed on that course.
The Moxon - Dennis partnership was almost rekindled on 66 minutes when the midfielder floated a great pass into the box. Dennis lunged to volley and Hinchliffe was completely beaten. It crashed against his post and Hussey helped it on its way.
Holy went full stretch to tip a Madden header past the nets after Brown had plopped it onto his head, and a near post touch from the forward from the corner was hooked away by Moxon as it spun dangerously on the line.
The electrics exploded in the press box, with everything plunged into darkness, and Stockport seemed to be happy to close down and keep the Cumbrians at bay. Gibson and Back looked to change that when they pushed on, and the eventual cross from the right back had to be dealt with as Dennis sniffed.
Wootton clipped one over from close range as a reverse touch from Collar pinged around, and Holy had to leap to save from Sarcevic when he swung a boot to send a Collar cross goalwards.
The lively Jack Stretton worked himself a chance as the board for four minutes of time added went up, but Hinchliffe had judged the angles well and that made it an easy save to complete.
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Goals
Stockport County - Hippolyte (20), Wootton (57)
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Bookings
Carlisle United - Back (73), Gibson (85)
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Teams
Stockport County - Hinchliffe, Wright, Horsfall, Madden (c) (Crankshaw 83), Collar, Brown, Croasdale, Wootton, Hippolyte (Sarcevic 83), Hussey, MacDonald (Johnson 69). Subs - Jones (gk), Palmer, Rydel, Jennings.
Carlisle United - Holy, Whelan, Feeney (c), Mellish, Back, Guy (Sho-Silva 78), Moxon, Harris (Stretton 46), Armer, Dennis, Gibson. Subs - Kelly (gk), Charters, Ellis, Bollado, Idehen.
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Match officials
Referee - Benjamin Speedie
Assistant Referee 1 - Ian Smedley
Assistant Referee 2 - Mark Cunliffe
Fourth Official - Aaron Jackson
Observer - Mark Haywood
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Attendance - 8,418 (1,116)