Port Vale made it two wins in two in the Leasing.com trophy and picked up their first away win of the season at Moss Rose.
Kieran Kennedy had the first chance of the game, when James Gibbons sent a corner back into the box where Kennedy connected with a header but the Silkmen’s keeper was able to comfortably collect the ball.
Mark Cullen had the next effort of the game in the 6th minute, having a shot saved after Richie Bennett picked him out on the edge of the box.
The hosts were next to come close to finding the game’s opening goal, as a ball was sent into the Vale six-yard box and asking questions of the defence, but Shaun Brisley flicking the ball towards Scott Brown who was able to gather it.
Brown was called into action again soon after, as a cross was curled into the box and Jacob Blyth rose highest to flick a header towards the far post, but Brown made a brilliant low save to keep the game level.
In the 16th minute the Silkmen took the lead, Charles-Cook sent the ball long from his own box and the ball ended up making its way all the way into the Vale area where it was picked up by Joe Ironside who slotted the ball into the back of the net.
With 15 minutes of the half remaining, Ironside nearly doubled his tally for the night and doubled his sides lead, curling an effort towards goal but it deflected past the bottom right corner and out for a corner.
The Valiants came close themselves to drawing level a few minutes later, as Gibbons sent a ball to the back post where Bennett volleyed it across the face of goal and Mark Cullen just couldn’t get there to make it one a piece.
In the 34th minute the Vale did get their goal however, Scott Burgess marking his debut for the club with a goal to remember.
A Vale corner was cleared but Burgess picked up the ball on the edge of the box where he drilled it low and hard towards goal and found the bottom corner to tie things up.
Vale’s leveller was almost instantly cancelled out, another long ball caused problems for Kennedy who was beaten by Ironside for the ball, before the forward dinked it around Brown for an open goal only to be denied by an excellent sliding challenge by Shaun Brisley.
The second period started with a bang for the Vale, with Richie Bennett putting the Valiants in front with a strike from 30-yards out just five minutes into the half.
Bennett was given time on the ball and lined up the shot from very far out and drilled an attempt towards goal, it clipped a Macclesfield man on the way towards goal and wrong-footed the keeper who could only watch as the ball found the bottom left corner.
10 minutes later Luke Joyce nearly brought the Silkmen level with an own goal, a free-kick was sent into the box and deflected off of Joyce and towards goal but Brown was able to make the save.
Ryan Lloyd came close to getting his first goal in a Vale shirt, driving into the box and hitting a hard and high effort towards goal, but was denied by Charles-Cook with 64 minutes on the clock.
Bennett very nearly got a second 30-yard goal, being set up from a free-kick which he hit first time and forced a good save with 20 minutes to play.
The Valiants did extend their lead soon after however, with Jordan Archer, playing his first game back from injury, pacing down the right wing before playing a delicate ball into the path of Jake Taylor.
The youngster on loan from Nottingham Forest took a touch before dispatching a very tidy finish into the far side netting from a difficult angle to get his first goal for the club.
The Silkmen were able to pull another goal back in added time as Theo Archibald cut onto his left and drilled the ball into the top left from 25-yards out, but the Vale were able to see out the game for all three points.
Macclesfield Town: Charles-Cook, Clarke, Ironside, Stephens, Horsfall, O’Keeffe (45’ Archibald), Blyth (72’ Osadebe), Ntambwe, Fitzpatrick, Rose, Cameron (62’ Welch-Hayes).
Unused Subs: Evans, Gnahoua, Kirby, Gomis.
Port Vale: Brown, Crookes, Joyce (68’ Oyeleke), Kennedy, Gibbons, Lloyd, Burgess (90’ Hurst), Brisley, Taylor, Cullen (45’ Archer), Bennett.
Unused Subs: Maddison, Worrall, Pope, Smith.