Nine-men Boro failed to extend their lead at the top of the Barclays Under-21 Premier League Second Division table after a heavy 3-0 defeat against Reading.
The hosts were forced to play with ten men for 80 minutes after Robbie Tinkler's early dismissal, and goals from Tariqe Fosu and a Harry Cardwell brace put the Royals in command.
Boro's dismal afternoon was then made even worse when captain Jonny Burn received a second yellow card late on, with the setback meaning Boro remain two points clear at the summit.
Paul Jenkins made one change from the side that beat West Brom 3-1 on Monday, with Ryan Brobbel returning to the starting line-up.
That meant youngster Harry Chapman dropped to the bench, with striker Brad Fewster - fresh from his two goals at the Hawthorns - again playing on the right flank.
Boro showed first inside two minutes with Fewster receiving the ball out wide, and he cut inside and lashed a shot just wide of the post.
There was huge controversy on 11 minutes as defender Tinkler was shown a straight red card after bringing down Reading attacker Fosu.
That decision sparked a touchline spat between the Reading coach and a spectator, with Tinkler pleading his innocence and claiming he got a touch on the ball.
Winger Junior Mondal was sacrificed as Boro brought on defender David Atkinson to restore their shape in defence.
Reading should have made their numerical advantage count on 19 minutes as the lively Fosu cut inside and crossed for Bogdan Vastsuk, but the unmarked Royals striker headed over from five yards out.
On the half hour mark Fryer was called upon again, with midfielder Jake Sheppard drilling a goal-bound shot that was held at the second attempt.
Boro continued to compete across the pitch and broke out on 35 minutes, with Lewis Maloney firing over.
The breakthrough came on 41 minutes as Fosu lashed home from close range after his initial shot was saved by Fryer, and then Andre Bennett heroically blocked another effort.
It was harsh on a Boro side still aggrieved by Tinkler's red card, with Jenkins equally unimpressed with referee Paul Brown's first-half display.
After the break it was Boro who threatened first, with Brobbel cutting in from the left and firing in a shot that was saved by Reading stopper Lewis Ward.
Approaching the hour mark the Teessiders should have drawn level when Maloney's cross was met by Burn - but his header cannoned off the inside of the post and was hacked to safety.
But at the other end Reading doubled their advantage shortly after, with Rob Dickie also rattling the woodwork with a header but Cardwell was on hand to net the Royals' second.
The visitors then appeared happy to defend their two-goal lead, and while Boro turned to youngster Chapman, they were restricted to long-range efforts with Maloney again testing Ward.
Conor Shaughnessy then fired high and wide for the visitors as the clock ticked down, before Fryer pulled off another stunning stop to deny Fosu.
But the rout was completed shortly after as Liam Kelly pulled the ball back to Cardwell, who made no mistake close range - before Burn was dismissed for a second yellow card late on.
Boro: Fryer, Tinkler, Jackson, Burn (c), Bennett, Maloney, Kitching (Chapman 66), Mondal (Atkinson 16), McAloon, Brobbel, Fewster. Subs not used: Pears, Weledji, Morelli
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