Macclesfield edged closer to relegation from the Football League after slipping to a narrow defeat by Port Vale.
The hosts dominated the first half, with both Louis Dodds and Tom Pope heading against the crossbar.
Ross Draper's shot was handled in the area by Doug Loft, but George Donnelly was unable to make the most of the opportunity for the Silkmen, hitting his penalty over the crossbar.
Adam Yates then prodded home Vale's late winner from close range.
That means just one point picked up out of a possible 18 for former Vale boss Brian Horton's Macc, who are now three points adrift of safety.
Their last win was against Vale, who they beat 2-1 at Moss Rose on New Year's Eve - and they have not won in 19 league games since.
VIEW FROM THE DRESSING ROOM
Port Vale manager Micky Adams told BBC Radio Stoke:
"It's been a nice couple of wins. We're delighted with it and, after our first-half performance, I think we deserved it.
"We were disappointed to come in at half-time without a goal on the board but, having said that, could they get any worse? Probably not. You could tell that Brian Horton had a few harsh words with them.
"The good thing about Adam Yates is that regardless of how he's playing he keeps going and today he's had a bit of luck and got on the end of one."
Macclesfield manager Brian Horton told BBC Radio Manchester:
"In the first half, we weren't at the races. We looked apprehensive, nervous and frightened to get hold of the ball.
"I'll never blame anyone for missing penalties because not everybody wants to take them.
"I took them all my career and I missed some in big games.
"He [George Donnelly] said he went to rifle it and he's completely mis-hit it. He said he'll take the next one if we get one in the next game."
Full Time The referee blows for the end of the match.
Outswinging corner taken from the right by-line by Chris Shuker, clearance by Marcus Marshall.
Corner taken by Sam Wedgbury, clearance made by Chris Shuker.
Arnaud Mendy is adjudged to have handled the ball. Shot comes in from Chris Shuker from the free kick.
Stuart Tomlinson takes the free kick.
Booking The referee books George Donnelly for unsporting behaviour.
George Donnelly challenges Adam Yates unfairly and gives away a free kick.
Assist on the goal came from Tom Pope.
81:44 Goal scored
Goal - Adam Yates - Port Vale 1 - 0 Macclesfld Adam Yates finds the net with a goal from inside the six-yard box to the bottom right corner of the goal. Port Vale 1-0 Macclesfield.
Tom Pope produces a left-footed shot from deep inside the penalty area and strikes the post.
Corner taken by Sam Wedgbury from the left by-line played to the near post.
Substitution Ben Williamson replaces Sean Rigg.
Tom Pope fouled by Colin Daniel, the ref awards a free kick. Direct free kick taken by Sam Morsy.
Substitution Paul Marshall leaves the field to be replaced by Chris Shuker.
Substitution Anthony Griffith leaves the field to be replaced by Sam Morsy.
Substitution Jonathan Bateson replaces Matthew Hamshaw.
Power penalty missed by George Donnelly.
Penalty awarded for a foul by Doug Loft on Ben Mills.
Free kick crossed left-footed by Paul Marshall.
Booking The referee cautions Ross Draper for unsporting behaviour.
Ross Draper challenges Marc Richards unfairly and gives away a free kick.
Doug Loft produces a right-footed shot from close range which goes wide of the right-hand upright.
Foul by Nathaniel Brown on Marc Richards, free kick awarded. The free kick is delivered left-footed by Paul Marshall from right channel.
Outswinging corner taken by Matthew Hamshaw from the right by-line, free kick awarded for a foul by Nathaniel Brown on Marc Richards. Free kick taken by Stuart Tomlinson.
Corner from the right by-line taken by Matthew Hamshaw, Stuart Tomlinson makes a save.
Corner taken right-footed by Matthew Hamshaw from the right by-line, Nathaniel Brown takes a shot. Save by Stuart Tomlinson.
Inswinging corner taken from the left by-line by Matthew Hamshaw, save made by Stuart Tomlinson.
Shot by George Donnelly from deep inside the penalty area misses to the right of the target.
Anthony Griffith gives away a free kick for an unfair challenge on Ross Draper. Free kick taken by Nathaniel Brown.
Inswinging corner taken left-footed by Paul Marshall, Ross Draper makes a clearance.
Outswinging corner taken by Paul Marshall, Marcus Marshall manages to make a clearance.
Doug Loft delivers the ball, Sean Rigg takes a shot. Save by Richard O'Donnell.
Outswinging corner taken by Paul Marshall.
Centre by Doug Loft, Sean Rigg has a headed effort at goal from close in which goes wide left of the goal.
Adam Yates challenges Colin Daniel unfairly and gives away a free kick. Free kick crossed by Matthew Hamshaw, save by Stuart Tomlinson.
Louis Dodds produces a right-footed shot from inside the area that clears the bar.
Matthew Hamshaw takes the inswinging corner, John McCombe manages to make a clearance.
Sean Rigg gives away a free kick for an unfair challenge on Nathaniel Brown. Direct free kick taken by Richard O'Donnell.
A cross is delivered by Colin Daniel, George Donnelly takes a shot. Stuart Tomlinson makes a comfortable save.
Corner taken by Paul Marshall played to the near post, Ben Mills makes a clearance.
The game restarts for the second half.
45:00 +3:22 Half time
Half Time It is the end of the first-half.
Paul Marshall takes a inswinging corner from the right by-line to the near post, clearance by Carl Tremarco.
Corner taken by Paul Marshall, Tom Pope takes a shot. Clearance made by Arnaud Mendy.
Paul Marshall delivers the ball from the free kick left-footed from left channel, clearance made by Nathaniel Brown.
Substitution Ben Mills joins the action as a substitute, replacing Matt Smith.
Foul by Matt Smith on John McCombe, free kick awarded.
Free kick awarded for a foul by Carl Tremarco on Louis Dodds. Paul Marshall sends in a cross, Louis Dodds takes a shot. Nathaniel Brown manages to make a clearance.
Ross Draper challenges Marc Richards unfairly and gives away a free kick. Direct strike on goal from the free kick comes in from Marc Richards.
Ross Draper challenges Anthony Griffith unfairly and gives away a free kick. Clayton McDonald restarts play with the free kick.
Corner from the left by-line taken by Paul Marshall, Nathaniel Brown manages to make a clearance.
The referee gives a free kick against Tom Pope for handball. Direct free kick taken by Richard O'Donnell.
Free kick awarded for a foul by Arnaud Mendy on Marc Richards. The ball is crossed by Paul Marshall, Tom Pope produces a header from deep inside the six-yard box which goes wide of the right-hand upright.
Unfair challenge on Tom Pope by Arnaud Mendy results in a free kick. Free kick taken by Paul Marshall.
Marc Richards is penalised for a handball. Indirect free kick taken by Matthew Hamshaw.
Paul Marshall takes a outswinging corner from the left by-line played to the near post, Nathaniel Brown manages to make a clearance.
Sean Rigg takes a shot. Save by Richard O'Donnell.
Sam Wedgbury challenges Paul Marshall unfairly and gives away a free kick. Free kick taken by Clayton McDonald.
The ball is sent over by Doug Loft.
Unfair challenge on Arnaud Mendy by Marc Richards results in a free kick. Free kick taken by Nathaniel Brown.
Corner taken by Paul Marshall, Nathaniel Brown makes a clearance.
Anthony Griffith concedes a free kick for a foul on Matt Smith. Sam Wedgbury restarts play with the free kick.
The referee blows for offside. Free kick taken by Richard O'Donnell.
Effort from deep inside the area by Marc Richards misses to the right of the goal.
Outswinging corner taken by Paul Marshall.
Paul Marshall takes a inswinging corner from the right by-line to the near post, Carl Tremarco makes a clearance.
Nathaniel Brown concedes a free kick for a foul on Marc Richards. The free kick is delivered left-footed by Paul Marshall from right wing, Ross Draper manages to make a clearance.
Louis Dodds takes a shot.
The ref blows the whistle to start the match.
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