The Silkmen fell to a comprehensive 3-0 defeat at The Jonny-Rocks Stadium as goals from Luke Varney, Conor Thomas and Ryan Broom secured all three points for Cheltenham.
Macc held their own for much of the first half, with Joe Ironside coming close to putting Macc ahead just before the 20 minute mark; but his header was deflected behind Scott Flinders' goal.
Cheltenham took a while to grow into the game, with their first chance of note coming on after half an hour as Chris Hussey fired over the crossbar after Charlie Raglan's cut back.
Macc would have another chance through Arthur Gnahoua before falling behind, but his effort was blocked by the Robins' back line.
Luke Varney netted the evening's opening goal, sliding the ball into an empty net after Ryan Broom played the ball across the six yard area.
Conor Thomas then doubled Cheltenham's advantage on the hour mark as he stretched to divert the ball past Owen Evans.
Macc responded well to this setback and had the ball in the net as substitute Virgil Gomis turned Jak McCourt's cross into the net, but he was adjudged to have done so from an offside position and the goal was chalked off.
This would prove costly as the Robins added their third just three minutes later as Ryan Broom took the ball around Owen Evans to seal the points for Cheltenham.
Evans then produced a fantastic late save to keep out Alex Addai from close in.
Cheltenham would have the ball in the net once more as the game fizzled towards its conclusion, but Jonte Smith saw his effort ruled out for offside.
Smith would come close once more, but he clipped the post with a late right footed shot.
Cheltenham Town Macclesfield Town
1. Scott Flinders 1. Owen Evans
2. Sean Long 4. Jak McCourt
3. Chris Hussey 5. Fiacre Kelleher
4. Ben Tozer 6. Theo Vassell
5. Charlie Raglan 7. Arthur Gnahoua (Virgil Gomis 68')
7. Conor Thomas 9. Joe Ironside
11. Ryan Broom (Rohan Ince 87') 11. Theo Archibald
20. Gavin Reilly (Alex Addai 77') 12. Miles Welch-Hayes
21. Jake Doyle-Hayes 14. Connor Kirby
26. Jacob Greaves 16. Corey O'Keeffe
32. Luke Varney (Jonte Smith 71') 20. Emmanuel Osadebe
Cheltenham Town: Chris Clements, Will Boyle, George Lloyd, Rhys Lovett (GK)
Macclesfield Town: Ben Stephens, Reice Chales-Cook (GK), Fraser Horsfall, Brice Ntambwe, David Fitzpatrick.