The Iron's Under-18 side were narrowly edged out 6-5 by Chesterfield in an entertaining away contest in the Youth Alliance League on Saturday morning.
Despite Harry Jessop's hat-trick and further goals from Luca Chadli and Levi Gallimore, the Iron were defeated, as Chesterfield held out for the victory.
However, United showed fantastic character throughout the second half to bring the scoreline back to 6-5 after being 6-2 down. They fell just short of earning a draw, as the Spireities did enough for the three points come the final whistle.
Chesterfield started brightly, attacking from the first minute, however solid, collective defending from the Iron prevented them from taking the lead.
United then had their first opportunity of the game five minutes in when Joey Dawson was fantastically played through the middle, but as he bared down on goal, his shot was saved by the goalkeeper down in the right corner.
Five minutes later, Chesterfield came forward on the right flank. The full-back made a run down the wing and forced a corner after his attempted cross was deflected behind.
From the resulting set-piece, the Spireities worked the ball well to create an opening, but Charlie Barks threw his body on the line to block the final effort away.
Chesterfield continued to press in search of a goal. However, good defensive play from the Iron and Harry Baker denied them a way through.
But it was almost United who took the lead. On 25 minutes, Cameron Wilson unleashed a venomous volley from the edge of the area which forced the opposing goalkeeper into making a fine save, as he tipped the ball over the crossbar.
Then, it was Ben Crosher in the Iron goal who was forced into action. The keeper had to be alert to make a smart save down low to prevent the Chesterfield attacker from scoring.
However, just seconds later, the Spireites did open their account. They gathered possession back in midfield and countered through the middle and the striker produced the end product into the corner of the goal 27 minutes in.
With half-an-hour on the clock, Chesterfield broke away again, but this time, the final shot was put wide of the target.
Five minutes later they did managed to double their lead when the striker again was on the money to head home past Crosher after a cross from the wing was whipped in dangerously.
The Iron searched for a way back into the game and almost found it a couple of minutes later when Chadli latched onto a through ball, however his effort was dragged just wide of the post.
The Iron did finally make the breakthrough they deserved just before half-time, as Chadli curled a spectacular effort into the far corner of the net from the edge of the box to make it 2-1 going into the interval.
As the teams emerged for the second half, Chesterfield capitalised on a loose ball with 47 minutes on the clock to extend their advantage once again, as the right-winger broke free and slotted past Crosher.
Levi Gallimore then came on to replace Dawson and he almost had an instant impact, but his shot was blocked.
On 55 minutes, the Iron scored again to bring the scoreline back to 3-2. Jessop netted his first goal of the game, as he calmly turned in a Chadli cross.
Two minutes later, United were nearly back on level terms. Jessop looked lively and knicked in to intercept an intended pass by the goalkeeper, but somehow, the keeper recovered brilliantly to save the shot in the corner of the goal.
Then, with just over an hour played, Chesterfield made it 4-2. The central midfielder picked up possession in the centre of the park and dribbled superbly past four players before neatly putting the shot away into the back of the net.
Not long after, the Iron surged forward in an attempt to reduce the deficit. Levi Gallimore got down the flank, before he crossed low for Jessop, but his effort went wide.
70 minutes in, the Spireites had their fifth. The winger picked up the ball on the edge of the area, produced a good turn of pace to beat his man and hit his shot into the net.
The Iron weren't finished yet. With over 15 minutes still to play, Levi Gallimore got on the end of a Jessop cross to make it 5-3.
This fired United in action and Gallimore was at the centre of proceedings once again as he was brought down in the box not long after scoring. Jessop stepped up to take the penalty and was on the scoresheet for the second time, as he made no mistake from 12-yards.
However, Chesterfield put daylight between the teams again, scoring with ten minutes left to extend the lead to 6-4.
The Iron still had fight left in them and reduced the score back to one when Jessop completed his hat-trick on the 89th minute, slotting into the corner of the net.
There were four added minutes at the end of the 90 played. The Iron pushed for an equaliser, but Chesterfield held on.
Despite the final result, the Iron can still be pleased with their performance, putting in a fine shift to almost snatch a point at the end.
The Under-18's will be back in action against Hartlepool in two weeks' time.
Scunthorpe United: Crosher, Baker, Lobley, D.Gallimore, Barks, Kemp, Wilson, Shrimpton (Silva, 79), Dawson (L. Gallimore, 47), Jessop, Chadli.