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."