The Silkmen were undone by former hero Richie Barker's two late goals to deny Paul Ince of a dream start in the dugout.
Colin Heath's brilliant lob gave Macclesfield the advantage before Giles Coke fortuitously levelled for the Stags.
Captain Dave Morley thought he had grabbed the winner with less than ten minutes to go, but Barker headed in an equaliser and blasted in a penalty at the death to break Macc hearts.
Heath was preferred to Spencer Weir-Daley and new signing John Murphy to partner Matthew Tipton up front, with Ian Brightwell at the centre of a five man defence.
Barker showed his aerial threat as early as the second minute, beating Jonny Brain to Danny Reet's left wing cross to head over the bar.
Macc's first chance fell to Tipton who drilled into the side netting from the left channel. Two minutes later Heath almost found the net but his drive was parried wide after an excellent Martin Bullock run down the by-line.
Barker had another chance for Mansfield in the 20th minute when he swivelled to volley a loose ball but Brain was equal to it and palmed behind.
Kevin McIntyre came closest to scoring in the first half when his bullet header from Tipton's cross bounced back off the upright. Bullock was on hand to put the rebound away but was immediately flagged offside.
The first half ended goalless but with the Silkmen on top and unlucky not to have broken the deadlock. Mansfield rarely threatened apart from a few breaks and Barker's strength from set pieces.
Heath scored the opening goal four minutes into the half, with a thunderbolt which arced into the roof of the net from out on the right after good link up play with Tipton.
John Mullins nearly equalised moments later when his precise side foot from the edge of the box bounced back off the foot of the post and was cleared.
The Silkmen seemed to go into their shell after scoring and it was no surprise when the Stags levelled. Barker's header was well parried by Brain, but the ball bounced back into the net off Coke, who knew little about it.
McIntyre should have done better in the 72nd minute when he was played in by Heath, but on his wrong foot he skewed his shot well wide.
Paul Ince then made two changes - introducing loanee striker John Murphy for Tipton and Andrew Teague for the tired Ian Brightwell. The veteran sweeper had a superb game though and his positioning and reading of the game had saved the defence on a number of occasions earlier in the game.
Spencer Weir-Daley came on for Heath in the last ten minutes and soon afterwards Macc were back ahead.
A deep cross from the right was nodded back into the box by Teague and Dave Morley was on hand to fire in unmarked from ten yards.
The lead wasn't to last long though as back up the other end Alan Sheehan's cross from the right found Barker in too much space and his header was too strong for Brain, who could only palm it up into the top corner. The burly striker's muted celebrations were a stark contrast to the delirium of the visiting supporters behind the goal, but they would end up even happier by the final whistle.
With the game looking like it would finish even, things went from bad to worse for Macc.
Sheehan again got a cross in from the left which was flicked on by substitute Michael Boulding and hit the arm of Dave Morley. The referee instantly pointed to the spot and everyone in the ground knew what was to followt. Barker stepped up and blasted the kick in off the left hand post for his 10th of the season and to give his side their first away win of the campaign.
Macc pumped a few long balls forward in the final minutes of injury time but never created anything more and for the third time this season scored two at home but ended up losing.
The zero in the wins column is getting more alarming week by week, but they deserved more after such a strong performance, at least for an hour. Wrexham next week will be a tough test for Ince's first away game in charge and Macc will need to up their game even more to get a result at the Racecourse.
Andrew Brinkhurst
