A battling second-half display failed to rescue Cheltenham after Macclesfield struck twice before the break.
The Silkmen took the lead on 27 minutes as Ricky Sappleton pounced on a Colin Daniel flick-on to thread a shot between the legs of keeper Scott Brown.
John Rooney doubled their lead on 43 minutes with a stunning 25-yard volley.
Elvis Hammond lifted the Robins with a neat turn and shot inside the box on 69 minutes, but Macclesfield held on for their first-ever win at Whaddon Road.
Under-pressure Martin Allen's Cheltenham have now slumped to 18th in League Two after a five-game run in which they have picked up just one point and shipped 13 goals.
Cheltenham boss Martin Allen: "It's disappointing to have not won at home since the first game of the season, but it doesn't depress me.
"Julian Alsop is a real asset to us. He gets in people's faces. He showed passion and commitment and his spirit is a lesson to others.
"But we didn't take our chances. We had the majority of play again but came up short in the final third.
"There were players playing with knocks that shouldn't have been out there. And, when the left-back Lee Ridley went off injured, that was very disruptive.
"Credit to a lot of players who are getting iced in there. They probably won't train now until Thursday because they are carrying knocks."
Live text and stats
Friday, 16 October 2009
League Two
Home Team
Score
Away Team
Time
Cheltenham
1-2
Macclesfield
FT
(HT 0-2)
Hammond 69
Sappleton 27
Rooney 43
Cheltenham
01 Brown
03 Ridley (Low 11)
05 Townsend
06 Diallo
08 Gallinagh
27 Eyjolfsson (Alsop 56)
02 Bird
07 Pook
23 Artus (Lewis 79)
09 Richards
11 Hammond
Substitutes
40 Richardson,
10 Hutton,
17 Low,
28 Rose,
19 Denton,
22 Lewis,
39 Alsop
Macclesfield
01 Brain
03 Tremarco
05 Brown
16 Brisley
02 Reid
07 Bell
14 Rooney (Draper 74)
17 Daniel
20 Bencherif
09 Sinclair
22 Sappleton (Wright 74)
Substitutes
13 Veiga,
10 Reed,
08 Draper,
15 Bolland,
11 Wright,
12 Wilson,
23 Tipton
Ref: PhillipsAtt: 2,930
CHELTENHAM
MACCLESFIELD
Possession
Cheltenham49%
Macclesfield51%
Attempts on target
Cheltenham6
Macclesfield4
Attempts off target
Cheltenham8
Macclesfield7
Corners
Cheltenham6
Macclesfield1
Fouls
Cheltenham8
Macclesfield14
Final Result
Full Time
90:00+5:06 The final whistle goes and the game is over.
90:00+1:04 Free kick awarded for an unfair challenge on Izak Reid by Michael Pook. Izak Reid restarts play with the free kick. Emile Sinclair delivers the ball. The official flags Ben Wright offside. Scott P Brown takes the free kick.
89:52 Hamza Bencherif challenges Elvis Hammond unfairly and gives away a free kick. Direct free kick taken by Scott P Brown.
87:46 Emile Sinclair takes a shot. Scott P Brown makes a comfortable save.
87:01 Theo Lewis challenges Lee Bell unfairly and gives away a free kick. Carl Tremarco takes the direct free kick.
84:27 The ball is swung over by David Bird, Nathaniel Brown manages to make a clearance.
81:45 Foul by Lee Bell on Michael Pook, free kick awarded. Michael Pook takes the direct free kick. David Bird takes a shot. Comfortable save by Jon Brain.
81:19 Ross Draper gives away a free kick for an unfair challenge on Justin Richards. Scott P Brown takes the direct free kick.
80:50 The ball is crossed by David Bird, clearance by Hamza Bencherif.
79:57 Unfair challenge on Carl Tremarco by Theo Lewis results in a free kick. Direct free kick taken by Jon Brain. Ben Wright gives away a free kick for an unfair challenge on Michael Townsend. Scott P Brown takes the free kick.
78:54 Substitution (Cheltenham) makes a substitution, with Theo Lewis coming on for Frankie Artus.
77:37 Free kick awarded for an unfair challenge on Shaun Brisley by Frankie Artus. Free kick taken by Nathaniel Brown.
77:12 David Bird produces a cross, Julian Alsop takes a shot. Comfortable save by Jon Brain.
76:23 Hamza Bencherif produces a left-footed shot from just outside the box that misses to the right of the target. Nathaniel Brown concedes a free kick for a foul on Julian Alsop. Michael Pook restarts play with the free kick.
74:26 Inswinging corner taken by Frankie Artus, Jon Brain makes a save. Drissa Diallo challenges Ben Wright unfairly and gives away a free kick. Izak Reid takes the direct free kick.
72:53 Jon Brain takes the free kick.
72:53 Substitution Ben Wright joins the action as a substitute, replacing Reneil Sappleton.
72:53 Substitution Ross Draper comes on in place of John Rooney.
72:53 The official flags Justin Richards offside.
72:34 Free kick awarded for an unfair challenge on Michael Pook by Lee Bell. Michael Pook takes the direct free kick.
71:17 Julian Alsop fouled by Nathaniel Brown, the ref awards a free kick. Direct effort from the free kick comes in from David Bird.
68:18 Assist by Michael Pook.
68:18 GOAL - Elvis Hammond:Cheltenham 1 - 2 Macclesfield Elvis Hammond fires in a goal from deep inside the penalty box low into the middle of the goal. Cheltenham 1-2 Macclesfield.
64:07 The ball is crossed by Colin Daniel, Michael Townsend manages to make a clearance. Hamza Bencherif takes a shot. Scott P Brown makes a comfortable save.
61:56 Elvis Hammond fouled by Izak Reid, the ref awards a free kick. Free kick crossed by David Bird, clearance by Lee Bell.
59:58 Julian Alsop takes a shot. Save by Jon Brain. Corner taken right-footed by David Bird, save made by Jon Brain. Inswinging corner taken by Frankie Artus, Shaun Brisley manages to make a clearance.
59:11 Colin Daniel sends in a cross, clearance made by Drissa Diallo.
58:32 Elvis Hammond has shot on goal from just outside the box which goes wide of the right-hand upright.
57:13 Shot from long range by Frankie Artus misses to the left of the net.
56:18 Lee Bell concedes a free kick for a foul on Andy Gallinagh. Michael Townsend takes the direct free kick.
55:48 The referee gives a free kick against Julian Alsop for handball. Jon Brain takes the direct free kick.
54:59 Substitution Julian Alsop on for Holmar Orn Eyjolfsson.
54:59 The ball is sent over by Colin Daniel.
53:05 Lee Bell produces a right-footed shot from just outside the penalty area that goes harmlessly over the target.
51:03 Free kick awarded for an unfair challenge on Elvis Hammond by Nathaniel Brown. Free kick taken by Michael Pook.
47:31 Emile Sinclair takes a shot. Comfortable save by Scott P Brown.
46:49 Michael Townsend gives away a free kick for an unfair challenge on Emile Sinclair. Lee Bell takes the direct free kick.
45:32 Elvis Hammond fouled by Nathaniel Brown, the ref awards a free kick. Frankie Artus has a direct shot on goal from the free kick.
45:01 The second half begins.
Half Time
45:00+2:13 The match has reached half-time.
45:00+1:29 Andy Gallinagh takes a shot from just inside the penalty box which clears the bar.
42:29 GOAL - John Rooney:Cheltenham 0 - 2 Macclesfield John Rooney scores a brilliant goal from outside the box to the top left corner of the goal. Cheltenham 0-2 Macclesfield.
41:55 Corner taken right-footed by Lee Bell from the right by-line to the near post, Frankie Artus manages to make a clearance.
41:13 The ball is swung over by Colin Daniel, clearance made by Drissa Diallo.
40:05 Centre by Joshua Low, save made by Jon Brain. Frankie Artus takes a outswinging corner to the near post, clearance by Nathaniel Brown.
38:31 The ball is delivered by David Bird, Justin Richards takes a shot. Save by Jon Brain.
37:23 Justin Richards is ruled offside. Free kick taken by Jon Brain.
36:30 Reneil Sappleton gives away a free kick for an unfair challenge on Drissa Diallo. Michael Townsend restarts play with the free kick.
36:01 The offside flag is raised against Reneil Sappleton. Free kick taken by Scott P Brown.
34:41 Michael Pook concedes a free kick for a foul on Emile Sinclair. Izak Reid takes the direct free kick.
33:40 Colin Daniel takes a shot from just inside the penalty box which clears the bar.
31:55 David Bird crosses the ball.
31:13 Frankie Artus is penalised for a handball. Direct free kick taken by Jon Brain.
29:53 Unfair challenge on Shaun Brisley by Justin Richards results in a free kick. Jon Brain takes the free kick.
29:11 The offside flag is raised against Reneil Sappleton. Scott P Brown takes the free kick.
28:09 Michael Pook has an effort at goal from outside the box which goes wide right of the goal.
26:05 Assist by John Rooney.
26:05 GOAL - Reneil Sappleton:Cheltenham 0 - 1 Macclesfield Reneil Sappleton scores a goal from inside the box low into the middle of the goal. Cheltenham 0-1 Macclesfield.
23:35 Corner taken right-footed by David Bird, Shaun Brisley manages to make a clearance.
21:31 Izak Reid sends in a cross.
20:45 The referee blows for offside against Elvis Hammond. Jon Brain takes the free kick.
20:19 The ball is crossed by Holmar Orn Eyjolfsson, Shaun Brisley makes a clearance.
16:57 Frankie Artus produces a cross.
15:38 Michael Pook fouled by Lee Bell, the ref awards a free kick. David Bird restarts play with the free kick.
14:53 Reneil Sappleton has an effort at goal from the edge of the area that misses to the right of the target.
13:00 Elvis Hammond has shot on goal from just outside the area which goes wide of the right-hand upright.
11:24 Unfair challenge on Elvis Hammond by Nathaniel Brown results in a free kick. David Bird fires a strike on goal direct from the free kick.
10:05 Indirect free kick taken by Scott P Brown.
10:05 Substitution Joshua Low replaces Lee Ridley.
10:05 Reneil Sappleton is ruled offside.
8:34 Elvis Hammond has an effort at goal from deep inside the area missing to the right of the goal.
7:42 Effort from the edge of the area by Emile Sinclair goes wide of the right-hand upright.
7:06 Effort on goal by John Rooney from outside the box goes harmlessly over the bar.
6:38 The ball is sent over by Izak Reid, clearance by Michael Townsend.
5:57 The referee blows for offside against Elvis Hammond. Free kick taken by Jon Brain.
4:12 Elvis Hammond is flagged offside by the assistant referee. Jon Brain restarts play with the free kick.
3:51 The ball is delivered by Frankie Artus, save made by Jon Brain.
3:13 Corner taken left-footed by Frankie Artus from the left by-line to the near post, Carl Tremarco makes a clearance.
1:43 The ball is crossed by Holmar Orn Eyjolfsson, Jon Brain makes a comfortable save.
0:53 The ball is delivered by Lee Ridley, Izak Reid makes a clearance.
0:00 The game kicks-off.
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Cheltenham 1-2 Macclesfield 
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