Bolton Wanderers Under-21s threw away a 3-0 half-time lead as a late collapse saw them fall to a last-minute defeat away at Coventry City on Monday afternoon.
In a convincing first half display, the young Whites took control of the fixture thanks to a Kaiyne Woolery brace and Jamie Thomas free-kick.
However braces from George Thomas and Bassala Sambou saw the Sky Blues turn the game on its head, as three goals inside the final ten minutes saw Bolton suffer an unlikely defeat in dramatic circumstances.
Kaiyne Woolery captained Wanderers as they took on Coventry City at The Alan Higgs Centre, while Harry Campbell returned in goal.
Lawrie Wilson and Filip Twardzik were also both named in the young Whites' starting XI along with Jon Ceberio, with Under-18s goalkeeper Jake Turner named on the bench.
Facing off in treacherous conditions, Wanderers were fortunate not to fall behind early on as Coventry forward Lateef Elford-Alliyu side-footed wide when well-placed from the game's first opening.
The hosts continued to attack early on as Harry Campbell was twice called into action, first denying Coventry forward Bassala Sambou from close-range, before tipping George Thomas' curling 25-yard free-kick around the post.
However, the Whites fought back and began to take control proceedings as they were rewarded with the game's opening goal from their first attack shortly after the quarter-hour mark through Kaiyne Woolery.
Receiving the ball in midfield, the forward embarked on a solo-run forward before powerfully firing low into the bottom corner, beyond the grasp of goalkeeper Konrad Skuza, from the edge of the box.
Buoyed by taking the lead, Bolton continued to threaten as Jamie Thomas saw a strong appeal for a penalty turned down before Filip Twardzik fired narrowly over the crossbar from range.
The Trotters did manage to double their lead on the half-hour mark however, as Kaiyne Woolery netted his second of the game.
Turning well on the edge of the box to beat his man with a clever dummy, the forward burst into the area before drilling past Skuza across goal into the bottom corner.
Continuing to pass the ball around well, Wanderers looked to extend their lead further with J.Thomas twice forcing Skuza into saves after finding space in the area.
It was third-time lucky for the Welshman just before the break, as he curled a 25-yard free-kick into the top corner to give the Whites a convincing lead at the break following a commanding display.
Picking up where they left off following the restart, Jon Ceberio should have made it 4-0 after running onto J.Thomas' cutback, however the Spaniard failed to keep his strike down as he fired harmlessly over the crossbar when well-placed and left unmarked inside the area.
Skuza denied Bolton once more moments later as he steered Channing Campbell-Young's rifled effort away from goal after the midfielder was picked out by Lawrie Wilson.
At the other end, Campbell saved well to keep out Jay Albini's well-struck strike from the edge of the box shortly before the hour-mark.
However, Albini had better luck moments later as he created Coventry's first goal with an inch-perfect cross, leaving G.Thomas with a simple finish as he headed home into the corner.
J.Thomas continued to threaten for the Trotters as they remained in control despite conceding, but the forward saw Skuza tip his drilled effort from an acute angle wide, before gathering his tame chipped strike soon after.
With ten minutes left on the clock, Coventry began to throw bodies forward as they looked to produce a late comeback, with Campbell doing well to rush off his line and twice deny G.Thomas having seen him cut inside to penetrate the Wanderers defence.
But there was nothing Campbell could do to stop the Sky Blues netting their second in the 84th minute as Sambou tapped home Ronee Hendricks' low cross.
Rattled at seeing their lead reduced, the Whites looked nervy at the back and were punished further as Coventry netted an unlikely equaliser just two minutes later - G.Thomas coolly slotting home into the corner from the penalty spot.
And their shock victory was sealed in stoppage time as Sambou slammed home into an empty net after G.Thomas had rounded Campbell, much to the disbelief of the Bolton squad.
Bolton: Campbell, Wilson, Garratt, Twardzik, Finney, Phillips, Perry, Campbell-Young (Cvetko 80), Woolery, Ceberio (Newell 60), Thomas.
Unused substitutes: Turner, Spooner.