Millwall exited the FA Youth Cup at the Third Round stage on Monday night after Tottenham Hotspur were 2-1 winners after extra time at The Den.
Billy Mitchell's 34th-minute thunderbolt looked to have given The Lions all they needed to set up a Fourth Round tie with Arsenal, but J'Neil Bennett's 94th-minute equaliser denied Millwall what would have been a shock - but deserved - victory.
Rodel Richards, though, scored in extra time to win the game for Spurs.
The Lions pushed high in the opening stages and fashioned the first chance of the game on six minutes, but Samuel Skeffington's effort was deflected behind.
With 21 minutes on the clock Spurs threatened for the first time as Richards danced his way into the box - his shot was blocked, with Troy Parrott's follow-up then saved by Joseph Wright. Armando Shashoua then found a way inside the penalty area, but his attempted cross was cleared behind.
On 34 minutes, in spectacular fashion, Millwall took the lead as Mitchell crashed in a piledriver off the underside of the crossbar from 30 yards out.
Reuben Duncan then narrowly missed the target from a free-kick as The Lions looked to double their shock advantage. Just a minute into the second-half The Lions had an opportunity to extend their lead, but Skeffington was closed down well as he attempted to shoot from 12 yards out.
George Alexander tried the audacious with 51 minutes on the clock, trying a scissor kick on the volley from 20 yards out, but he fired wide. Alexander then had another attempt on goal which Joshua Oluwayemi initially saved, but as the ball looked to be slipping underneath his grasp and into the net, it bounced up on to the roof of the net, going behind for a corner.
Dilan Markanday had Tottenham's best effort of the night on 54 minutes, but he headed wide from around six yards out. Markanday then looked to slot home from Bennett's cross, but Wright made a fantastic save.
Spurs were beginning to turn the screw and the lively Bennett was causing problems - he had the ball in the net shortly before the hour-mark, but he was ruled offside. Paris Maghoma then found the lower tier behind the goal with 19 minutes remaining.
On 74 minutes Alexander picked out Jayden Davis at the back post, but his effort, unmarked, from six yards out somehow went wide. With a shock on the cards, Parrott turned and unleashed a vicious effort towards goal three minutes from time, but Wright tipped over the crossbar superbly.
With Millwall defending bravely, their hearts were broken three minutes into six of stoppage-time as substitute Bennett hooked home from close range.
Four minutes into extra-time, Spurs nudged themselves in front after Parrott beat Wright to the ball - he squared to Richards, who had the easiest of tasks of slipping the ball into an empty net.
The heroic Lions continued to press, however, with Alexander hitting the post after Oluwayemi had initially saved his shot. The end-to-end action then continued with Maurizio Pochettino through on goal, but Wright made himself big and saved to stop the game going beyond Millwall's reach.
Four minutes into the second-half of extra-time the ball fell at the feet of Harry Taylor on the edge of the six-yard box, but Dennis Cirkin heroically blocked what looked to be an otherwise certain equaliser. Taylor tried his luck again seconds later, but his effort was deflected into the side-netting.
With nine minutes remaining substitute Sean O'Brien tried his luck on the volley, but the ball looped over the crossbar. At the other end Markanday had a clear strike on goal, but Wright saved well.
Markanday had the ball in the net into four minutes of stoppage-time, but he was correctly ruled offside.
Millwall: Wright, West, Tiensia, B. Mitchell, Muller (Abdulmalik 98'), Topalloj, Skeffington, Duncan (Barton 85'), Alexander (A. Mitchell 97'), Taylor, Davis (O'Brien 105'). Subs not used: Fanshawe.
Scorer: Mitchell 34'
Booking: West, Alexander, Tiensia, Barton
Tottenham Hotspur: Oluwayemi, Statham (Bennett 54'), Cirkin, White, Lyons-Foster (Tainio 85'), Binks, Markanday, Shashoua (Pochettino 78'), Parrott, Maghoma, Richards (Okedina 105'). Subs not used: Kurylowicz.
Scorer: Bennett 90+4', Richards 94'
Booking: Shashoua, Binks, Maghoma, Tainio
Referee: Mr R. Adams