Cheltenham Town slipped to their fifth home reverse of the campaign as Martin Allen's winless run extended to six games.
Two goals of real quality handed Macclesfield a two-goal cushion at the break; the first a team effort to savour and the second a stunning strike by 18-year-old John Rooney - a volley his goal his older brother Wayne would be proud to have in his portfolio.
Elvis Hammond pulled one back with 20 minutes remaining, but the Silkmen defended manfully to preserve their slender advantage in the closing stages of this one to claim the points both sides craved.
This was Macclesfield's first-ever success at the Abbey Business in seven attempts. For Martin Allen, the search for that elusive second win on this ground since the opening day success against Grimsby Town goes on.
TEAM NEWS: Boss Allen welcomed back David Bird, Lee Ridley (both calf), Drissa Diallo (hip), Frankie Artus (back on a month's loan from Bristol City) and Holmar Eyjolfsson (international duty) to his starting line-up after last weekend's injury-ravaged defeat by Accrington Stanley. Barry Hayles missed out, picking up a hamstring injury in training while Sam Cox had returned to parent club Tottenham Hotspur earlier in the week. Romone Rose, David Hutton and Josh Low took their places on the bench.
Eighth minute: Rooney fired over the first opening of night with eight minutes on the clock. Then he teed up Ernie Sinclair a moment later, but the Macclesfield striker rifled his angled effort into the side-netting.
9: Cheltenham's first opportunity of the evening fell to Hammond, who should have done better from eight yards when he collected Michael Pook's mis-hit to stab a shot wide of the right post.
11 SUBSTITUTION: Ridley limped out of this one within 11 minutes with a re-occurrence of the calf injury which forced him out of last weekend's game at the Crown Ground. Low was sent on to deputise at left back.
12: Bird fizzed a 20-yard free-kick a couple of inches past the left upright.
14: Hammond twisted away from Silkmen skipper Nat Brown to fashion a shooting chance from 18 yards, but again the striker lacked composure, blasting it well wide of the target.
15: The next chance was put wide by Ricky Sappleton after he had been played in by Rooney with quarter of an hour played.
27 GOAL: Cheltenham Town 0-1 Macclesfield Town
The game's first moment of quality came mid-way through the first half, produced by Macclesfield to break the deadlock after a somewhat scrappy but entertaining opening to the match. The visitors had enjoyed a good passage of possession when Hamza Bencherif picked up play down the right, squaring for Lee Bell who dinked it in from the edge of the box. Sinclair turned it into the path of Sappleton and the big striker bundled a strike through Scott Brown to hand his side the lead.
34: Daniel wasted the chance to extend the lead after picking up Pook's loose ball 30 yards from goal, only to blast one well over.
39: Richards met Bird's centre from the right-hand side with a decent enough header, but it was straight at goalkeeper Jon Brain, who claimed it with both hands.
43 GOAL: Cheltenham Town 0-2 Macclesfield Town
The second arrive two minutes before the break, and it was a strike of genuine class by Rooney which will live long in the memory. It came about after Low had conceded a corner which Bell thumped in from the right. Artus headed it clear, but only as far as Rooney who lasered an unstoppable left-footed volley from 25 yards beyond Brown to notch his first league goal of the season.
45: Gallinagh sent one into the bowling green after Eyjolfsson had flicked Bird's corner from the right into the midfielder's path.
HALF TIME: 0-2
47: Artus lifted a 20-yard free-kick out of the ground.
48: Right back Izak Reid cut one back into Rooney's path after making a run into the box, but Brown managed to get a hand on it to deny the striker.
54: Bell fired over after Justin Richards lost possession inside his own half.
56 SUBSTITUTION: Julian Alsop was pressed into action nine minutes after the restart at the expense of Eyjolfsson. Bird dropped back to right back, and Richards to right midfield. Not for the first time this season, the big man's introduction galvanised his side into some better attacking play.
59: Hammond narrowly missed the target with an 18 yarder, then Alsop was denied by a diving stop from Brain after the striker released a low shot from a tight angle.
69 GOAL: Cheltenham Town 1-2 Macclesfield Town
Cheltenham forced themselves back into the contest with a little under 20 minutes remaining and it was a moment of magic from Alsop which started the move, back-heeling into Richards' path down the left. He picked out Pook in a central position, who nudged it into Hammond to apply the finish past Brain to register his fifth of the campaign.
74 DOUBLE SUBSTITUTION: Perhaps surprisingly Macclesfield replaced their front line with 74 minutes played, removing Rooney and Sappleton for Ross Draper and Ben Wright respectively. Macclesfield compromised their threat to Brown's goal by finishing the game with numbers behind the ball to preserve their slender advantage.
79 SUBSTITUTION: Boss Allen made his final switch with 11 minutes to play, replacing Artus with striker Theo Lewis who slotted into central midfield behind the front two.
83: Brain spilled Bird's low drive from 20 yards after Pook had touched a free-kick into the Cinderford-born midfielder's path.
FULL TIME: 1-2
CHELTENHAM TOWN (4-4-2): Brown; Eyjolfsson (Alsop 56), Diallo, Townsend, Ridley (Low 11); Bird (c), Gallinagh, Pook, Artus (Lewis 79); Richards, Hammond. Subs not used: Hutton, Denton, Rose, Richardson (Gk).
MACCLESFIELD TOWN (4-4-2): Brain; Reid, Brisley, Brown (c), Tremarco; Sinclair, Bell, Bencherif, Daniel; Sappleton (Wright 74), Rooney (Draper 74). Subs not used: Reed, Wilson, Veiga (Gk), Bolland, Tipton.
REFEREE: D Phillips
ATTENDANCE: 2,930 (107 from Macclesfield)
Murry Toms at the Abbey Business Stadium
