It was heartbreak for the Boro late on at the Leasing.com Stadium, as Macclesfield struck twice in the dying embers to collect all three points in Cheshire.
Radcliffe started brightly and threatened early on when a deflected Danny Greenfield effort won the visitors a corner.
The resulting delivery caused problems in the Macclesfield box, with a dangerous cross finding a Radcliffe head before Jordan Hulme drilled the ball across the six-yard box.
Michael Nottingham attacked the delivery, forcing goalkeeper Christian Dibble into an excellent save with his leg to keep the scores level.
Macclesfield responded with a long-range effort that stung the gloves of Tom Donaghy, who did well to push the ball away from danger.
The subsequent cross was then comfortably cleared for a goal kick.
Radcliffe came close again late in the half when a loose pass allowed Hulme to win possession and release Rio Clegg.
The number 17 found himself with time and space 15 yards from goal but fired over the crossbar with a golden opportunity going begging.
The visitors continued to threaten after the interval.
Radcliffe won a throw-in high up the pitch, substitute Josh Seary launching the ball into the area.
Roscoe flicked it on and Hulme held off his marker before laying the ball back to the defender.
The resulting effort flashed across the six-yard box, sparking a scramble before Macclesfield eventually cleared.
Another huge opportunity fell to Radcliffe when Lois Maynard’s long ball split the Macclesfield defence and found Hulme.
The captain drove towards goal one-on-one with Dibble, but the goalkeeper once again stood firm, keeping out the initial effort before the follow-up was also squandered.
Macclesfield soon began to find more space in dangerous areas.
Osbourne collected the ball on the edge of the box and curled an effort around Donaghy, only to see his strike come back off the post.
Radcliffe continued to carry a threat at the other end.
Brad Jackson, introduced in the first half, picked up possession on the right and delivered towards Clegg.
After controlling the ball as a Macclesfield defender slipped, Clegg created room on the edge of the box, but Cameron Borthwick-Jackson recovered brilliantly to block the shot.
Macclesfield then enjoyed a spell of pressure, with Donaghy saving from Ammar Dyer before Adan George fired over the bar on the 68-minute mark.
Moments later, Clegg was presented with another opportunity when the ball fell kindly to him inside the area.
With Dibble advancing and the ball bouncing awkwardly, Clegg attempted to find the far corner, but the Macclesfield goalkeeper reacted superbly to turn the effort around the post.
The Silkmen continued to push forward, with Jon Ustabsai breaking quickly before laying the ball off to Luke Duffy.
The forward’s effort was once again denied by Donaghy’s outstretched leg, maintaining the end-to-end action without the opening goal.
However, Radcliffe finally made the breakthrough soon afterwards.
Hulme showed excellent skill to flick the ball over his defender before drilling a dangerous delivery across the box.
Macclesfield initially cleared, but the ball fell to Jon Taylor just inside the 18-yard, and he made no mistake, firing beyond the goalkeeper to give the visitors the lead on 78 minutes.
Macclesfield’s response was immediate, levelling the terms only seconds after the action got back underway.
The Silkmen sent the ball forward, putting the Radcliffe defence under instant pressure to find Duffy, who kept his composure to fire a low effort beyond Donaghy.
With momentum firmly behind the hosts, Macclesfield continued to press for the winner, and were rewarded for their attempts.
Lincoln McFayden found space down the left and carried the ball into the penalty area before delivering a low cross across the face of goal.
Duffy was perfectly positioned to meet the delivery and calmly tapped home to complete the turnaround for his second of the afternoon.
Despite looking destined to take something from the game, Macclesfield’s clinical finishing and a series of saves from Dibble proved decisive when the referee’s full-time whistle was sounded.
Radcliffe will be back in action this Tuesday as they remain on the road to lock horns with Hereford at Edgar Street.
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