Two first half mistakes that resulted in goals gave Town a mountain to climb, before an early second half penalty ruined any chances of a comeback and allowed Guiseley to claim a comfortable victory.
The clash pitted current Captain Josh Falkingham against former Captain Danny Ellis as Town favourites past and present faced off in the dugout.
Town were handed a scare inside the first two minutes when Hussain won possession high up the pitch before racing through on goal and hitting the cross bar.
Despite the hosts trying to find their feet, another shaky moment at the back lead to Town falling a goal down as Waddington closed down Taylor-Widdowson's clearance and slotted into an empty net.
Gus Steele prevented it being two not long after with a goal line clearance, though Sam Clark was proving a threat at the other end and would have levelled with a lofted finish if not for some impressive one on one goalkeeping.
With just under ten minutes until the break Clark and Nimick combined again, but the visiting stopper again denied Town's number ten.
Despite Town coming back into the game, Jake Young found a bit of space in the Town area and, after seeing his initial finish bounce back to his feet via a Town defender, netted Guiseley's second.
Six minutes after the restart it was 3-0 to Guiseley after Hussain emphatically dispatched a spot kick after a coming together in the Town box.
It could have been more when Taylor-Widdowson's clearence fell straight to Young, but the keeper brought down the visiting striker outside the box, receiving a yellow card for the foul.
The fourth goal eventually arrived 20 minutes from time as a cross from the right was only parried as far as the Young, who stroked home his second of the night.
Young claimed his hat-trick eight minutes later, curling into the bottom right corner from the edge of the area to cap an impressive night for the striker.
Falkingham's side did get a goal to show for their night's work as Richardson broke down the right and pulled back to Jake Little, who teed up Sam Clark to finish!
Town U18s: Taylor-Widdowson, Weal (Johnson 71), Ingoldsby (Whyte 67), Mutch, Steele (Dobson 45), H Clark, Little, Nimick, White, Clark, Richardson
Subs not used: Kellett, Calvert
Goals: S Clark 86
Guiseley: Lambton, Straker, Newall, Jackson, Hall, Brayshaw, Hussein, Starcenko, Young, Coker, Waddington