Logan Briggs and Reece Evans gave City a 2-0 lead, but three goals either side of the break from Joshua Chapman, Bailey Cadamarteri and Rio Shipston completed the turnaround for Wednesday as the Foxes fall out of the competition in the fourth round.
There was only one change from the side the beat Wolverhampton Wanderers in the last round, as Evans came in to replace the injured Will Alves, who was sadly withdrawn in injury time, with a season-ending injury.
City's youngsters faced a Wednesday outfit who hadn't lost since September of last year, an unbeaten streak spanning eight games heading into Friday's fixture, which included a penalty shootout victory in the last round of the cup against Barnsley.
It was the hosts who looked more dangerous from the off, controlling most of the possession against a Leicester side who were hoping to stretch the Owls' with a 4-3-3 formation.
Sheffield's early control led to them having the first chance of the game six minutes in, when Sean Fusire laid the ball into the path of Jarvis Thornton, whose, fierce effort was just over Dilon Addai's net.
The Foxes' resilience started allowing them chances of their own, and went close in the 14th minute through an almost perfectly executed counter-attack.
Following a strong challenge from Jahmari Lindsay, the full-back continued to drive, before the ball eventually found its way to Evans, who fired wide under pressure from Jack Hall in the Wednesday net, but was saved his blushes when he looked across to see the linesman's flag raised for offside.
Minutes later, the deadlock was broken by Leicester's youngsters through Briggs. Picking up the ball on the edge of the box, the midfielder look to have had his advances into the box nullified, that was until he unleashed a left-footed rocket, that flew past the Sheffield 'keeper into the back of the net, hitting the underside of the bar on its way in.
Over the next 20 minutes, both sides looked to score, with Leicester looking to strengthen their lead, while Wednesday were hoping to not let the visitors take a strong lead, and five minutes from half-time, the home side's worries were realised.
In the 39th minute, Lindsay broke down the left wing, and cut into the box before picking out Evans at the back post with a low cross in front of goal, and the striker tapped home to give the Foxes a two-goal lead.
However, moments before the break, Wednesday were given a lifeline. A corner into the box wasn't dealt with by City's Under-18s and Chapman was on hand to half the deficit from close range.
The goal just before the interval sparked the hosts back into life, and only three minutes from the restart, they were back level. Cadamarteri took aim from the edge of the box and let loose a powerful right-footed effort, which had Addai beaten, reminding City's youngsters a tough lesson to not rest on your morals.
The comeback was then complete by Sheffield when Shipston was brought down in the box by Tom Wilson-Brown. Stepping up to convert his own penalty, the midfielder had the confidence to wait for Addai's decision before sliding the ball into the bottom left corner.
In an attempt to shake things up, two changes were made as Josh King and Jack Lewis were introduced. The injection of fresh energy needed paid off for Leicester when King came close to equalising with almost his first touch of the evening, but was denied by a smart stop from Hall.
In the dying moments, Leicester attempted to throw the kitchen sink at Wednesday's backline, but the Owls stood firm, and City's Under-18s cup journey would go no further.
Major moment - The turning point...
The hosts scored two goals in nine minutes to confirm the turnaround.
Leicester's youngsters didn't see much of the ball in the opening stages, but did find themselves 2-0 up. This hard work was to be undone by an impressive Wednesday comeback through goals from Chapman, Cadamarteri, and Shipston.
Who impressed? - Jahmari Lindsay
Jahmari Lindsay assisted Reece Evans' first half goal at Hillsborough Stadium.
Despite being on the losing end of the cup tie, the full-back looked more than capable of holding his own on the stage set before him on Friday evening. Showing strength at the back, the No.3 was also a threat going forward, and assisted Evans' first half goal.
Where do we stand - Out of the cup
The Foxes return to league action where they currently sit 12th in the standings after nine games.
Now eliminated from the FA Youth Cup, the Foxes focus on their league form, where they currently sit bottom of the U18 Premier League South Division with seven points.
Coming up - Aston Villa (A)
Trey Nyoni in action against Sheffield Wednesday.
Following the defeat, City's Under-18s must regroup and go again, when they travel to Aston Villa for U18 Premier League South action on Saturday 21 January (11am kick-off).
City: Addai; Grist, McAlinney, Wilson-Brown, Lindsay; Cartwright (c) (Ali 75'), Briggs, Nyoni (Lewis 65'); Joseph, Evans, Richards (King 63').
Sub not used: Cook, Weeks, Thomas, Javaid.
Goals: Briggs 17', Evans 39'.
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