Norwich City Under-21s suffered a late defeat at the hands of Exeter City in the Under-21 Premier League Cup.
Tom Dean scored with just seconds left on the clock for the travelling side when it looked as though the game was petering towards a goalless draw.
Harmony Okumo was also dismissed for the Canaries late in the game.
The first opportunity of the night fell to the Norwich trialist who was denied by the feet of Harry Lee after 10 minutes.
As the first half progressed, a couple of positive City moves created chances to go ahead. The first was cut out by a timely defensive intervention with Adian Manning firing over soon after.
A succession of corner-kicks for Exeter City looked as though they may cause trouble but Caleb Ansen remained composed in the Norwich goal.
Amani Richards looked lively for the visiting team and looked for a penalty late in the first half when he was bundled over by Lucien Mahovo. However, the referee waved away the claims.
Errol Mundle-Smith had a chance late in the half to nudge Norwich in front but could only find the side-netting.
The experienced Kevin McDonald offered a good presence in the middle for Exeter for the hour that he played.
Both sides enjoyed good spells in control in the first half with no real opportunity of note until Dan Ogwuru's left-footed shot was straight at Lee in the 63rd minute.
Chances soon started to flow for both sides with Charlie Wilson having his header cleared off the line at one end before Jake Richards hit the post from close range at the other.
An excellent cross from Harmony Okwumo found Brandon Forbes but he could only head over as the game entered the final 10 minutes.
Mundle-Smith had another wonderful opportunity to steal a late win but his close-range header was over.
The missed opportunities would haunt City when Dean tapped home from close range late on.
Norwich remain winless in the Under-21 Premier League Cup while Exeter City top the group with 12 points.
Norwich City Under-21s: Ansen; Okwumo, Tomkinson, Warner (C) (Wilson h-t), Mahovo; Trialist (Ogwuru 60), Djedje; Springett (Forbes h-t), Manning, Bridge; Mundle-Smith
Unused subs: Finch, Chilvers
Bookings: Okwumo (61, 90+4), Djedje (86)
Red card: Okwumo (90+4)
Exeter City Under-21s: Lee; Cummins, James (C), Cayless (Perkins 87), Beardmore (Edgecombe 76); Oakes, McDonald (Billington 58); A Richards, Dean, J Richards, Cutler (Wilson 76).
Unused subs: Shanahan
Goals: Dean (90+5)
Bookings: Edgecombe (80), Oakes (87), Cummins (89), J Richards (90+4)
HT: 0-0
FT: 0-1
Venue: Avant Training Centre
Referee: Ruebyn Ricardo