The 10 men of Norwich City suffered a disappointing 3-1 defeat to Middlesbrough at the Riverside Stadium on Wednesday evening.
After taking an early lead through Ashley Barnes, Norwich looked in full control until Borja Sainz was shown a red card after 30 minutes.
Just 13 minutes later, Norwich were behind as Marcus Forss and Emmanuel Latte Lath turned it around for Boro.
Lukas Engel added a third in the second half to seal the three points.
David Wagner had opted for an unchanged starting XI, with Marcelino Núñez returning from injury to take his place on the bench.
And it was the Yellows who started stronger, coming close to opening the scoring twice through Sainz and Barnes.
First, Sainz struck wide from the edge of the box after Seny Dieng had done well to force Dimi Giannoulis wide on the Greek full-back's 100th appearance for the club.
The 'keeper then punched away an effort from Barnes, again after Giannoulis had caused problems on the left.
However, it was just five minutes later that Barnes did get the opener. He prodded the ball home after miscuing his first effort from Gabriel Sara's pass.
Just as the game hit the half-hour mark, Norwich were reduced to 10 when Sainz was shown a red card after an off the ball incident with Jonny Howson.
Forss equalised seven minutes later as the hosts took control. Giannoulis couldn't get a firm enough contact on his clearance and Forss was able to poke home via the post.
Latte Lath nudged Boro in front two minutes before the break when he was able to take Matt Clarke's cross under control and slot the ball past Angus Gunn.
Núñez was introduced for Christian Fassnacht at the break as Norwich switched to a 4-3-2.
However, the 10 men were unable to force the play into Boro's half.
The home side would make it a two-goal cushion when Engel volleyed past Gunn in the 62nd minute.
Gunn was called upon again immediately after to turn away a powerful shot from Riley McGree.
One bright spot for the Canaries in a turgid second half was the appearance of Finley Welch from the bench in the closing minutes.
It was Welch's first taste of first-team football having featured in matchday squads in recent weeks.
Rotherham United are the visitors to Carrow Road at the weekend.
Middlesbrough: Dieng; Ayling (Dijksteel 69), McNair, van den Berg, Clarke, Engel; Forss (Gilbet 87), McGree (Azaz 80), Howson (C) (Barlaser 69), O'Brien; Latte Lath (Silvera 69).
Unused subs: Glover, Jones, Greenwood, Thomas.
Goals: Forss (37), Latte Lath (43), Engel (62)
Bookings: Forss (20)
Norwich City: Gunn; Stacey, Hanley (C) (Sørensen 70), Gibson, Giannoulis; McLean (van Hooijdonk 77), Sara; Fassnacht (Núñez h-t), Sainz, Barnes (Welch 87); Sargent (Gibbs 70).
Unused subs: Long, McCallum, Batth, Fisher.
Goals: Barnes (17)
Bookings: McLean (47)
Red Cards: Sainz (30)
HT: 2-1
FT: 3-1
Referee: Robert Madley
Venue: Riverside Stadium
Attendance: 23,545