THROUGH very testing conditions, Welling United showed their mettle to see off Chester in the first ever meeting between the two clubs.
Busy negotiations on the final day of the transfer window were a new experience for Welling manager Jamie Day but only one of his three deadline day signings started.
Harry Beautyman came close in the first minute but was just wide of the far post following a poor Chester clearance.
Another Wings attack saw Harry Cornick's shot blocked by Kevin McIntyre before a foul by the Chester midfield man earned him a stern admonishment.
McIntyre injured himself making a tackle and while Chester were dithering over their substitution, Welling broke away and scored.
Beautyman's long ball sent Cornick away and the AFC Bournemouth loanee showed great composure in tucking the chance beyond John Danby.
John Rooney, brother of the England talisman, looked dangerous in dead ball situations, with the swirling wind creating havoc, and a corner of his was headed on to the roof of the net by Ross Killock.
Joe Healy, who played a more central role alongside the tireless Jake Gallagher, had a shot saved after more poor defending had given him the space.
Injury to Connor McLaren meant that Welling had to make a change and he was replaced by Joe Obersteller.
Michael Kay was shown a yellow card for hauling down Oluwatobi Sho-Silva and it was the industry of the Welling debutant that created the Wings' second just before the break.
Chasing down a back pass, he tackled Danby before squaring to Ross Lafayette who slotted home from 10 yards.
Kay shot wide soon after the break then Healy charged down a Rooney shot before putting Welling three ahead.
Once again the Chester defence was slow and Healy was given plenty of time but still he had to pick his spot from 25 yards to beat Danby.
Just as Welling began to think the job was done, Chester pulled one back when debutant Matty Taylor got beyond the Welling defence to finish comfortably.
Beautyman dragged another shot wide before Killock was cautioned for a clumsy challenge.
Toby Ajala replaced Sho-Silva for his first Welling appearance but almost immediately Chester missed a great chance to pull another goal back.
A half cleared Chester corner fell for Jason Jarrett but he stabbed wide with the goal gaping.
Another Beautyman effort flew over as Welling continued to cause danger on the break whilst Doug Bergqvist and Blaine Hudson defended valiantly to ensure Lee Butcher did not have to make a save.
Substitute Kurtis Guthrie showed incredible skill to break out when he appeared to be trapped in the corner and Killock's rash tackle a foot outside the penalty area gave referee Darren England no option than to show him a second yellow card, and to dismiss him.
There was still time for Lewis Turner to get himself cautioned for a needless hack on Ajala as the Blues' frustration got the better of them but a late block by Jack Obersteller ensured that they failed to hurt Welling again in a meaningful manner and the Wings ran out deserved winners.
Welling United: Butcher, McLaren (Joe Obersteller 31), Jack Obersteller, Gallagher, Bergqvist, Hudson, Beautyman, Cornick (Guthrie 59), Sho-Silva (Ajala 63), Lafayette, Healy. Unused substitutes:Turner, Wakefield.