An undisciplined Macclesfield team handed Cheltenham three precious points as their game fell apart in front of a frustrated Moss Rose crowd.
The home side squandered a succession of early chances, and then paid the price for some slack defending, and an appalling goalkeeping gaff from veteran Alan Fettis.
The Macclesfield finishing was woeful, and they were clearly missing top scorer Jon Parkin. In the second minute, Paul Harsley thundered a half volley over the bar and later placed two other long distance shots into the stand.
The only chance on target came in the eleventh minute, John Miles playing a neat one two with Matthew Tipton, before seeing a close-range shot blocked by Shane Higgs. Cheltenham looked dangerous on the break, and in the 33rd minute Brian Wilson flew down the right forcing a magnificent diving save from Alan Fettis.
Macclesfield simply couldn't get the ball on target, skipper Tommy Widdrington twice blasting the ball against the advertising boards with veteran Mike Sheron going closer, but still not getting the ball on target.
Cheltenham looked stronger in the second half, Gavin Caines forcing Fettis to palm wide in the 54th minute before Martin Devaney powered another shot that produced a fine save.
But moments later, Cheltenham took the lead when John Finnigan planted neat cross onto the forehead of Steve Guinan, who nodded in off the far post.
The second goal came courtesy off a Christmas blooper from Fettis who allowed a Grant McCann shot to simply slip through his fingers.
Brian Horton threw on Tommy Rooney, cousin of Wayne, for his league debut, but Mac mustered little in the closing stages.
Only Sheron tested the keeper but his shot from the edge of the box deep in injury time was too little too late.