The Sky Blues exit the FA Youth Cup after falling to a narrow defeat against Southampton in the third round.
City had the better of the game and took the lead ten minutes from time through Aidan Dausch.
However, Southampton equalised through Dominic Ballard two minutes from time and the striker then found his second of the game towards the end of the first half of extra-time.
With five minutes left of the second half of extra-time, City though they had done enough to take the game to penalties when Elliot Betjemann struck a super free-kick into the top corner.
But, Southampton snatched the win, as Ballard picked up the ball inside of the area and completed his hat-trick a minute from time.
It was the Sky Blues who started the better of the two sides, as they applied pressure on the Saints from the off, winning a free-kick around 25 yards-out.
Elliot Betjemann stepped up to take the set-piece and he forced Southampton’s number one, Mohamed Adli into a fine save low down to his left.
City were looking to make their fast start count, and they created an opening when Isaac Moore found Tristen Batanwi in space and he surged forward, dropped his shoulder, and then forced Adli into a good stop.
It took 18 minutes for the visitors to find an opening and it fell for Sam Amo-Ameyaw, as he cut inside and bent the ball inches wide of Charlie Callaghan’s goal.
The Sky Blues though they had taken the lead at the other end when Charlie Manners’ shot was blocked on the line and then the follow-up strike from Moore was also cleared by a Saints defender on the line.
City continued to cause Southampton problems, especially down the left-hand-side and Batanwi, who skipped past two challenges to work his way into the area, before teeing up Moore on the volley, but he couldn’t steer his strike towards goal.
Southampton’s best chance came five minutes from time when they upped the ante and threatened Callaghan’s goal.
Firstly, captain Jem Hewitt watcher on as his shot was cleared off the line by Callum Perry and then seconds later Tyler Dibline forced Callaghan into his first save of the afternoon, as he got a strong hand on the shot from inside of the area.
Half-Time: Sky Blues 0-0 Southampton
The Sky Blues started the second half how they had begun the first, taking the game to Southampton and going close through a Charlie Manners strike, which went wide of goal.
Chances continued to fall City’s way, and a spectacular strike from Evan Eghosa from range almost found the top corner from 25 yards out.
From the resulting goal-kick, the Sky Blues intercepted Adli’s clearance and Kai Andrews saw his close-range effort stopped by the ‘keeper, before the visitors cleared their lines.
Callaghan was called into action for the first time in the second half, producing a good stop to deny Amo-Ameyaw from just inside of the area.
Eric Odihambo’s side continued to push for the opening goal and were keeping Adli in the Southampton goal busy, this time, a corner was cleared only as far as Batanwi, but his volley was gathered by the ‘keeper.
Another strike from distance followed, this time it was a free-kick from Elliot Betjemann which came back off the woodwork and spun behind for a goal kick.
Finally, the Sky Blues broke the deadlock with eight minutes left on the clock. Rio Grant’s ball over the top was perfect for Aidan Dausch and he took a touch and slotted the ball under Adli to put City in front.
The visitors had a chance at the other end to draw level four minutes from time, but Jimmy-Jai Morgan couldn’t direct his header towards goal.
However, a minute later, the Saints did have their goal, and it came from Dominic Ballard, as this time he was able to react quicker to Morgan’s shot, which fell to the number nine, and he found the equaliser.
Full-Time: Sky Blues 1-1 Southampton
The first chance of extra time came from Southampton, and it was an audacious effort from Kamari Doyle, as his free-kick from 30-yards-out skimmed the top of the bar.
Rylie Siddall was introduced after Charlie Manners couldn’t continue and he beat his man on the half-way line, then charged forward to pick out Dausch, but his shot deflected behind.
However, at the other end, with one minute left of the first half, Southampton completed the turnaround, with Ballard grabbing his second of the game, after getting on the end of a Lennie Davis cross.
Half-Time: Sky Blues 1-2 Southampton
City pushed for a leveller and a scramble inside of the Saints box, didn't fall for a Sky Blue shirt and Southampton were able to clear.
With six minutes left of extra-time, the visitors were reduced to ten men after Will Armitage was shown a second yellow card for a challenge on Evan Eghosa.
The resulting free-kick was struck by Betjemann and he produced a moment of magic, beating Adli from 25 yards out and drawing the Sky Blues level.
City pushed for a winner and it was Eghosa who was causing the Southampton back-line problems, this time getting in behind and producing a strike, which deflected over the bar.
However, it was heartbreak for the Under-18s as Ballard completed his hat-trick a minute from time, firing past Callaghan and confirming City's exit from the competition.
Full-Time AET: Sky Blues 2-3 Southampton
Yellows: Jimmy-Jai Morgan, Sam Amo-Ameyaw, Will Armitage x2, Charlie Finney, Aidan Dausch, Joe Wynne
Reds: Will Armitage
Goals: Aidan Dausch, Dominic Ballard x3, Elliot Betjemann
Sky Blues Xl: Charlie Callaghan (GK), Rio Grant, Lewys McCafferty (74’ Finney), Callum Perry (103’ Young), Joe Wynne, Tristen Batanwi, Evan Eghosa, Isaac Moore (C), Charlie Manners (95’ Sydall), Elliot Betjemann, Kai Andrews (67’ Dausch).
Subs: Fabian Vriesen (GK), Shay Young, Aidan Dausch, Charlie Finney, Jayden Smith, Rylie Siddall, Talon Shepherd.
Southampton Xl: Mohamed Adli (GK), Sonnie Davies, Will Armitage, Jem Hewlett (C), Jayden Meghoma, Kamari Doyle, Cameron Bragg, Jimmy-Jai Morgan, Sam Amo-Ameyaw, Dom Ballard, Tyler Dibling (79’ Andrews).
Subs: Henry Upstell (GK), Joe Andrews, Reggie Evans, Nicholas, Oyekunle, Ryan Chavez-Munoz, Tommy-Lee Higgs, Isac Bailey.