Lewis Wing scored a spectacular goal as Middlesbrough edged Premier League opponents Crystal Palace to reach the Carabao Cup quarter-finals.
Wing, making just his fifth start of the season, hit a swerving long-range effort beyond Vicente Guaita in first half stoppage-time to secure victory for manager Tony Pulis against his former club.
Both managers made eight changes to their sides that resulted in a game lacking in both quality and clear-cut chances.
Andros Townsend came closest to equalising for Palace late on but his 25-yard shot was pushed away by goalkeeper Dimitrios Konstantopoulos.
The narrow win sends Middlesbrough to the quarter-finals for the third time in seven seasons, where they can look forward to a home tie against League One Burton.
With both sides showing so many changes it was perhaps no surprise that the game lacked fluency, with little goalmouth action in the opening stages.
There was an injury blow for Middlesbrough on 28 minutes when Southampton loanee Sam McQueen went down clutching his knee and had to be carried off on a stretcher.
Far from disrupting Middlesbrough’s progress, the injury to McQueen seemed to galvanise the home side as they began to put some pressure on the Palace goal.
First Marcus Tavernier had a left-footed effort well blocked by Martin Kelly before Jordan Hugill sent a half-volley over from eight yards from George Friend’s left-wing cross.
But just as Middlesbrough’s first-half efforts looked to be going unrewarded, they took the lead in spectacular fashion in stoppage-time.
There looked to be little on when Tavernier laid the ball off to Wing outside the area, but the midfielder took a touch and hit a long-range effort that swerved into the top corner.
Palace struggled to create many clear-cut openings after the break against a well-drilled Middlesbrough side with the best defensive record in the Championship.
German midfielder Max Meyer had an opportunity when he broke clear in the area but could only shoot into the side netting. Townsend then drew a smart stop from Konstantopoulos late on when the Boro goalkeeper palmed the Palace winger’s curling effort away from danger.
Boro through to last eight – the stats
- Crystal Palace have now been eliminated from the League Cup by a side from a lower division than themselves in four of the last seven editions.
- Middlesbrough have eliminated a Premier League club from the League Cup for the first time since October 2015, when they beat Manchester United on penalties, also in the fourth round.
- Middlesbrough have now eliminated Crystal Palace in three of the four seasons they have met in the League Cup, only failing 2011-12.
- Middlesbrough manager Tony Pulis has eliminated a Premier League club from the League Cup while managing a non-top flight team for the first time since November 1996 when his Gillingham side knocked out Coventry City in a third round replay.
- Middlesbrough’s Lewis Wing has been directly involved in four goals in his last six games in all competitions (one goal, three assists), as many as his previous 22 combined.