Josh Benson netted a 92nd-minute winner as Barnsley won 1-0 at Championship Middlesbrough in the first round of the EFL Cup.
The hosts just shaded the game in terms of chances, and were on top for most of the second half, but the Reds showed great spirit and netted an epic winner.
Michael Duff made seven changes from the side that beat Cheltenham in the league on Saturday.
Jordan Helliwell and Clarke Oduor got their first action of the season and were used at right wing-back and left wing-back respectively. Jack Aitchison played just behind strikers Devante Cole and Aiden Marsh.
The hosts should have taken the lead in the second minute when a simple long ball played in Duncan Watmore who outpaced both Robbie Cundy and Conor McCarthy but was denied one-on-one by a good block from Jack Walton. Caolan Boyd-Munce shot wide of the bottom left corner from just outside the box in the fourth minute.
Barnsley settled down after being on the back foot early and Luca Connell curled a free-kick just over the bar from 25 yards on 19 minutes.
Walton touched over an attempted cross by Marc Bola which almost went into the top left corner then, at the other end, home goalkeeper Liam Roberts parried away a powerful and swerving long-range effort by Mads Andersen out of the path of the lurking Devante Cole.
Marsh should have put the visitors in front on the half-hour mark when a terrible backpass by Watmore put him clean through but his shot six yards out was blocked by Roberts.
Aitchison then shot wide of the bottom left corner from 12 yards out after a good move involving Marsh and Callum Styles.
Boro were on top at the start of the second half, with Paddy McNair getting barely any contact on a header from a corner when unmarked about ten yards out.
At the other end, Marsh shot into the side netting after being set free on the left. That was his last action as he and Aitchison were replaced by Aaron Leya Iseka, making his first appearance of the season, and Luke Thomas.
Centre-back McCarthy was replaced by midfielder Benson with the Reds changing to a 4-3-3 for the final 20 minutes.
Fabio Jalo, 16, was brought on and became the sixth youngest player in the club’s history.
Boro had chances late on as Walton impressively pushed a Dael Fry header out of the top left corner then easily caught a tame headed effort by Chuba Akpom.
The winner came after a good move on the right ended with Benson shooting from the edge of the box straight at the goalkeeper who fumbled back to him to tap in from close range.
Barnsley (3-4-1-2): Walton; Andersen, McCarthy (Benson 68mins), Cundy; Helliwell, Styles (Hondermarck 78), Connell, Oduor; Aitchison (Thomas 60); Cole (Jalo 78), Marsh (Iseka 60). Unused: Collins, Kitching, Moon, Ackroyd,
Yellow cards: McCarthy, Oduor.
Goals: Benson 90+2.
Middlesbrough (3-5-2): Roberts; McNair (Bilongo 60), Dijksteel, Fry; Smith, Boyd-Munce, Hackney, Gibson, Bola; Watmore (Forss 60), Finch (Akpom 60).
Unused: Daniels, Dodds, Fletcher, Kavanagh, Conteh, Sivi.
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