The Valiants suffered defeat on the road in a gruelling match as they travelled to Moss Rose to take on Macclesfield Town.
The Vale started well, controlling the play for the opening minutes of the game, with the 1,900 travelling Valiants making their voices heard and spurring on the team.
The. Hosts began to work their way into the game however, and piled on the pressure, winning three corners in a row as Vale remained solid at the back and prevent any attempts on goal.
Vale regained control of the game and Jake Taylor was brought down on the right just inside the Silkmen half.
David Worrall stood over the free-kick and delivered a dangerous ball into the box where Richie Bennett, back in the starting 11 after his goal against Morecambe, arrived at the front post to head into the far corner of the net and give the Vale the lead in the 12th minute
Vale remained on the front foot following the goal but with 20 minutes on the clock Theo Archibald made a darting run towards the Vale box where he cut inside and unleashed a vicious effort that was excellently saved by Scott Brown.
As the hosts continued to get more into the game they were kept at an arms lengths by the Vale defence who were denying Macclesfield any clear efforts on goal.
With 10 minutes of the half remaining Archibald forced another good save from Brown as he drilled a free-kick from 35-yards out hard and low with a late dip forcing Brown to get down before Bennett cleared the loose ball.
Vale could only keep the hosts out until the 39th minute however, as Emmanuel Osadebe fired the ball into Arthur Gnahoua who controlled it before firing a half-volley across goal and into the bottom corner to bring the game level.
The Silkmen continued to pile on the attack following their equaliser, but the Valiants were able to withstand the pressure and work their way back into the game after a strong start to the half.
Jake Taylor came close to putting the Vale back in front with the last kick of the half, finding space on the edge of the area before curling an effort towards goal but a solid save by Owen Evans denied late joy for John Askey’s side.
Vale had the first chance of the half with Bennett putting pressure on the backline, stealing the ball and drilling it across the face of gaol but nobody was there to put the ball in the back of the net.
It was Macclesfield who nearly took the lead however, former Valiant Theo Vassell winning a free header in the area but his attempt went wide of Brown’s right post.
With 15 minutes of the second period played, the game remained end to end with both sides desperate to find the goal that would put them in the lead.
It was the hosts who were able to find the breakthrough first, as Vale struggled to get the ball away a low ball was driven across the face of goal and it was Osadebe who got the all-important touch to send the ball into the back of the net and put his side ahead.
Leon Legge came millimetres from bringing the Vale back level, as he rose above everyone else to head towards goal from a Worrall corner, but his attempt just went over the bar.
As the game entered its final 10 minutes the Vale were relentlessly pressing to find an equaliser, with multiple set pieces and shots being sent towards the home sides goal but were being prevented from getting the goal they desired.
In the 90th minute the Vale continued to threaten the Silkmen goal and had an effort blocked over the bar from a corner scramble before Bennett’s strike from 30-yards flew over the bar, leaving the Vale unable to find an equaliser.
Macclesfield Town: Evans, Kelleher, Vassell, Gnahoua (83’ McCourt), Harris, Ironside, Archibald, Welch-Hayes, Kirby, O’Keeffe, Osadebe
Unused Subs: Clarke, Stephens, Charles-Cook, Gomis, Mtambwe.
Port Vale: Brown, Crookes, Gibbons (65’ Amoo), Joyce, Legge, Worrall, Pope (68’ Archer), Atkinson, Smith, Taylor, Bennett.
Unused Subs: Kennedy, Browne, Burgess, Brisley, Maddison