Nine-man Norwich City bowed out of the National League Cup following a 3-1 defeat against National League South side Braintree Town.
Finlay Corke was sent off five minutes before half-time, before Alan Domeracki was also dismissed in second-half stoppage time after picking up a second yellow card.
The hosts had taken an early lead, but Norwich responded well through Corke just five minutes later. However, the forward's dismissal proved a turning point, with Braintree making their numerical advantage count through goals either side of the interval.
Going into the fixture, the Canaries knew a victory was needed to secure their place in the quarter-finals alongside Group B winners West Ham, who had already qualified.
Olly Lee made five changes to the side that beat Derby County at Pride Park the previous week. 17-year-old Harry Darbyshire-Came returned between the sticks, while Zach Baumann and Takudzwa Gwanzura were both handed their first starts of the season. Luke Chukwu and Finlay Oligbo also came into the starting XI.
With qualification still within reach, the hosts made the brighter start. Alfie Matthews saw an early effort fly narrowly over after Luke Towler was dispossessed on the edge of his own area.
Braintree's positive opening was rewarded moments later when Zack Hambury's long-range effort took a heavy deflection, wrong-footing Darbyshire-Came before bobbling into the net.
The setback sparked Olly Lee's side into life, and Norwich were back on level terms just five minutes later. Elliot Myles won possession high up the pitch before playing in Finlay Corke, who found the bottom corner despite Hughes getting a touch.
Chukwu almost completed the turnaround just 30 seconds later, cutting inside before seeing his effort well saved by the Iron goalkeeper.
Growing in confidence, the Canaries moved the ball around well before Baumann was released down the left. However, the Ukrainian youth international's low cross narrowly evaded the onrushing Corke.
Despite Norwich enjoying the better of the play, Darbyshire-Came was called into action after 25 minutes, producing an excellent save to deny Hambury a second goal of the evening.
The Canaries continued to threaten, and another flowing move on 35 minutes ended with Baumann firing narrowly over after excellent build-up play from Chukwu and Towler.
Norwich's task was made more difficult five minutes before the interval when goalscorer Corke was sent off following an off-the-ball incident. The hosts were then handed the opportunity to regain their lead from the penalty spot, with Matthews converting to make it 2-1.
Facing an uphill battle with ten men, Olly Lee looked to his bench in search of a way back into the contest, introducing Joseph Kipa and Jake Glossop shortly after the restart.
However, the changes were unable to prevent Braintree from extending their advantage, with Jake Dyer flicking home a cross at the near post just five minutes into the second half.
Luke Towler was denied by Hughes after being played through over the top in what proved to be the Canaries' best opportunity of the second half on 66 minutes.
Hambury thought he had added a second goal of his own, and Braintree a fourth, just three minutes later after following up Darbyshire-Came's initial save. However, the offside flag came to Norwich's rescue.
Vinnie Leonard, Botan Ameen and Reuben Cooper were all introduced in the closing stages as the Canaries searched for a way back into the contest, but a comeback was not forthcoming.
Norwich were reduced to nine men deep into stoppage time when Domeracki received a second yellow card, as Olly Lee's side bowed out of the National League Cup in their debut campaign in the competition.
Despite the disappointment, the young Canaries can take plenty of positives from their run, having secured victories over National League opponents Hornchurch and Woking.
Braintree Town: Hughes; Namisi, Isaacson, Brown, Dyer; Hambury, Swann; Lewis, Matthews (C), Adebayo; Hubbard
Subs: Mensah, Clampin, Bolovan, Johnson, Thorpe, Senior, Sassi
Norwich City: Darbyshire-Came; Oligbo, Gwanzura (Leonard 73), Rowland (C), Özcan (Glossop 49); Towler, Domeracki; Baumann (Kipa 46), Myles (Cooper 79), Chukwu (Ameen 73); Corke
Subs not used: Collins, McCourt
Goals: Hambury (5), Matthews (41), Dyer (50); Corke (10)
Red Cards: Corke (40), Domeracki (90+2)
Half-time: 2-1
Full-time: 3-1
Venue: Rare Breed Meat Co. Stadium
Referee: Jason Richardson