Bolton Wanderers exited the FA Youth Cup at the third round stage, after coming out on the wrong side of a seven-goal thriller against Exeter City at St James Park.
Following a goalless first half the young Whites found themselves 2-0 down moments after the restart, courtesy of goals from Toby Down and Scott Merritt.
Cole Lonsdale halved the deficit with a deflected strike from range on the hour-mark, only for Ben Seymour to extend Exeter's lead from the penalty spot.
However, the young Whites fought back to draw level late on thanks to goals from Tyrell Palmer and Harry Brockbank.
But with extra-time looming, Mustafa Rehmi struck in the dying embers of the match to knock Bolton out of the competition.
Will Jaaskelainen started in goal for Wanderers, while Enock Likoy-Elumba was named in attack alongside Under-16s forward Matthew Fearnley.
There was a place on the substitutes’ bench for Alex Samizadeh, alongside Max Allen, Jake Turner and Tyrell Palmer with the trio having been involved with the Whites’ Under-21s against Nottingham Forest on Monday.
Facing off at St James Park, Wanderers were slow out the blocks as Exeter City looked to make home advantage count in front of a vocal crowd early on.
Looking to catch the Whites out with long balls over the top, the first chance of the night fell to the hosts as Frank Rosenwald found himself one-on-one after springing the offside trap.
However, Bolton captain Alex Honeyball made up ground to deny the forward a shot on goal with a last-ditch sliding tackle, with Scott Merritt putting the eventual rebound wide.
Ben Seymour was next to try his luck for Exeter as he looked to lob Will Jaaskelainen after drawing the goalkeeper outside of his penalty area, only for Harry Brockbank to get back to protect the unguarded net and clear the danger.
Seymour went close again moments later as he fizzed a low shot at goal from range, but Jasskelainen got down well to gather at the second attempt when under pressure.
Growing into the game as the first half wore on, the Trotters’ first opening of the night fell to Enock Likoy-Elumba.
But despite connecting with a cross after beating his man inside the penalty area, the forward was unfortunate to see his diving header narrowly clear the crossbar.
Looking to test the hosts through a series of corners, Wanderers created a number of nervy moments inside the Exeter area, but to no avail with the Grecians eventually managing to block and clear.
And it was from one of the subsequent counter-attacks that Exeter next threatened as they looked to outnumber the Whites on the break. However, Jaaskelainen read the situation well as he timed his run forward to gather.
At the other end, a wayward Exeter clearance fell kindly to Danny McKenna out on the left flank as the winger unleashed a fierce, first-time volley which fizzed narrowly wide of the post.
Cutting in from the right, Ryan White had the best half of the chance as he beat goalkeeper Kavanagh Keadell with a delightful curling strike from range, only to see his effort skim the crossbar and land on the roof of the net.
Encouraged by his close effort, White would twice again try his luck from similar positions, only to not connect as sweetly on either occasion as Keadell easily gathered one such strike, with his next effort harmlessly clearing the crossbar.
In between White strikes, Cole Lonsdale was unfortunate to drag an effort off-target, while at the other end Honeyball put his body on the line to block a stinging close-range Exeter strike following a goalmouth scramble.
The end-to-end nature of the half continued as Jaaskelainen was called into action once more with a fine low save to deny Rosenwald, while Bolton saw a penalty shout turned down as the two sides went in at the break with the scores goalless.
Despite looking to attack straight from the restart, the Trotters endured a nightmare start to the second half as Exeter took control of the tie with two quick-fire goals.
Defender Tony Down rifled the hosts ahead from the half’s first opening after being left unmarked in the box and connecting sweetly with Kyle Egan’s cross.
At the other end Likoy-Elumba headed narrowly wide when well-placed, and was quickly made to rue the miss as Exeter doubled their lead moments later following an error from Jaaskelainen.
Finding himself out of position, the Wanderers’ goalkeeper misjudged the flight of a chipped Merritt strike from the edge of the box, managing only to palm into his own net.
It could easily have been 3-0 moments later as Jordan Storey rattled the crossbar with a close-range strike following an Exeter corner.
But the Whites found themselves back in the tie on the hour-mark as Cole Lonsdale halved the deficit when a deflection on his long-range effort saw it fly beyond the grasp of Keadell into the top corner.
However, Bolton celebrations were short-lived as Seymour restored the host’s two-goal lead moments later from the penalty spot, powering home into the bottom corner despite Jaaskelainen’s best efforts.
Alex Samizadeh and Tyrell Palmer were introduced to the action midway through the half as the Trotters looked fight their way back into the game.
And the former almost made an immediate impact after losing his marker to connect with a deep free-kick at the far post, only to side-foot agonisingly wide.
However, both substitutes did manage to leave their mark moments later to ensure a nail-biting finish at St James Park as Palmer reduced the deficit once more.
Having seen Samizadeh fire against the crossbar from an acute angle, the winger was on hand to tap home the rebound from close-range.
Samizadeh was unfortunate not to add his own name to the scoresheet moments later with a spectacular effort, controlling a deep cross on the edge of the box before attempting an acrobatic overhead kick, only to see his strike blocked.
But the Trotters were not done yet as Brockbank poked home a deserved equaliser following a corner with just over five minutes left on the clock.
However, there was to be cruel heartbreak for Wanderers as Exeter re-took the lead moments later, Mustafa Rehemi side-footing home after being left unmarked in the box.
The Whites pushed forward in search of another late equaliser as Keadell pulled off a fantastic save to deny Likoy-Elumba what looked like a certain goal from close-range from Samizadeh’s low cross, while Bolton would see another effort hacked off the line.
But Exeter remained dangerous on the break, and could have easily extended their lead as Archie Collins struck the crossbar from range in stoppage-time, before Jaaskelainen tipped another strike onto the post.
Bolton won a number of late corners as they searched for another equaliser, but there was to be no late drama as Exeter held on to clinch victory as the Trotters exited the FA Youth Cup at the third round stage.
Bolton: Jaaskelainen, Everest, Lonsdale, Honeyball, Brockbank, Griffiths, White, Earing, Likoy-Elumba, Fearnley (Samizadeh 65), McKenna (Palmer 68).
Unused substitutes: Grivosti, Turner, Allen.