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Hayden Hackney's goal was just his second of the season in all competitionsChelsea missed a host of chances as Championship side Middlesbrough earned a slender advantage in the first leg of their Carabao Cup semi-final at a boisterous Riverside Stadium.
Hayden Hackney scored the only goal, opening up his body to slide home an Isaiah Jones cross in the first half.
Cole Palmer missed three presentable opportunities as Chelsea failed to score for the sixth time this season.
The second leg takes place on Tuesday, 23 January at 19:45 GMT.
Liverpool face Fulham in the other semi-final, with the final taking place at Wembley on Sunday, 25 February.
Palmer struggles as injury-ravaged Boro battle
Both sides came into the game with 12 first-team players unavailable and the situation worsened for Boro boss Michael Carrick when striker Emmanuel Latte Lath and left wing-back Alex Bangura were forced off in the opening 20 minutes.
Latte Lath had capitalised on a poor Levi Colwill header to get in behind the Chelsea defence and was caught on the ankle by Axel Disasi, but the referee waved away penalty appeals and there is no video assistant referee system in operation at this stage of the competition.
Palmer's first big miss came when experienced captain Jonny Howson gifted him the ball, 30 yards from the Boro goal. He drifted towards goals and looked to place in the corner but dragged wide.
Minutes later, Boro took the lead when Jones got in behind the Chelsea defence and twisted and turned Colwill, who struggled throughout, before his cross was turned in by Hackney, who had drifted off Moises Caicedo.
The goal was met with rapturous noise inside the Riverside, but the game soon returned to the familiar pattern of Chelsea attacks with Palmer turning over the bar after Enzo Fernandez's effort was spilled by Tom Glover.
Former Manchester City forward Palmer then saw another effort saved as he chopped in from the right, while Caicedo had a long-range effort fizz wide.
Chelsea dominated large periods of the second half too but failed to create any clear-cut opportunities, with a Noni Madueke header, which was comfortably saved, the closest they came.
Their recent investment can be highlighted by the fact that only two of the squad who played in an FA Cup tie against Boro in January 2022 are at the club this season, and while summer signing Palmer has been a shining light so far, this was a difficult night for the 21-year-old.
Mauricio Pochettino's side had scored in their past six games but must improve in the second leg if the Argentine boss is going to retain a chance of winning his first trophy in England at the end of February.
Among Premier League sides, only Bournemouth and Nottingham Forest (32 each) have lost more games than Chelsea (31) in all competitions since the start of last season, while no team have lost more away from home than the Blues (21) during that period.
Victory for Boro, who have suffered six defeats at home in the Championship this season, gives them hope of reaching the final of the competition they won 20 years ago.
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Middlesbrough
Squad number23Player nameGlover
Squad number3Player namevan den Berg
Squad number6Player nameFry
Squad number27Player nameEngel
Squad number11Player nameJones
Squad number4Player nameBarlaser
Squad number16Player nameHowson
Squad number24Player nameBangura
Squad number25Player nameCrooks
Squad number7Player nameHackney
Squad number9Player nameLatte Lath
Squad number5Player nameClarke
Squad number19Player nameCoburn
Chelsea
Squad number28Player namePetrovic
Squad number27Player nameGusto
Squad number2Player nameDisasi
Squad number6Player nameThiago Silva
Squad number26Player nameColwill
Squad number25Player nameCaicedo
Squad number8Player nameFernández
Squad number11Player nameMadueke
Squad number23Player nameGallagher
Squad number7Player nameSterling
Squad number20Player namePalmer
Squad number10Player nameMudryk
Squad number19Player nameBroja
Squad number42Player nameGilchrist
Line-ups
Middlesbrough
Formation 3-4-2-1
- 23Glover
- 3van den Berg
- 6Fry
- 27Engel
- 11Jones
- 4Barlaser
- 16Howson
- 24BanguraSubstituted forClarkeat 20'minutes
- 25Crooks
- 7Hackney
- 9Latte LathSubstituted forCoburnat 5'minutes
Substitutes
- 5Clarke
- 14Gilbert
- 19Coburn
- 28O'Brien
- 32Jones
- 48Kavanagh
- 49McCabe
- 52Bridge
- 57Bilongo
Chelsea
Formation 4-2-3-1
- 28Petrovic
- 27GustoSubstituted forGilchristat 90'minutes
- 2Disasi
- 6Thiago Silva
- 26ColwillBooked at 30mins
- 25Caicedo
- 8FernándezSubstituted forBrojaat 63'minutes
- 11MaduekeSubstituted forMudrykat 63'minutes
- 23Gallagher
- 7Sterling
- 20Palmer
Substitutes
- 10Mudryk
- 13Bettinelli
- 19Broja
- 36de Souza Eugênio
- 42Gilchrist
- 47Bergström
- 51Williams
- 68Golding
Live Text
Match ends, Middlesbrough 1, Chelsea 0.
Second Half ends, Middlesbrough 1, Chelsea 0.
Foul by Armando Broja (Chelsea).
Jonny Howson (Middlesbrough) wins a free kick in the defensive half.
Corner, Chelsea. Conceded by Hayden Hackney.
Foul by Moisés Caicedo (Chelsea).
Josh Coburn (Middlesbrough) wins a free kick in the defensive half.
Delay over. They are ready to continue.
Substitution, Chelsea. Alfie Gilchrist replaces Malo Gusto.
Delay in match because of an injury Matt Crooks (Middlesbrough).
Attempt blocked. Conor Gallagher (Chelsea) right footed shot from outside the box is blocked.
Offside, Middlesbrough. Josh Coburn is caught offside.
Attempt missed. Axel Disasi (Chelsea) left footed shot from the centre of the box is close, but misses to the left following a corner.
Corner, Chelsea. Conceded by Jonny Howson.
Attempt missed. Raheem Sterling (Chelsea) right footed shot from the centre of the box is close, but misses the top right corner. Assisted by Mykhailo Mudryk.
Attempt saved. Mykhailo Mudryk (Chelsea) right footed shot from outside the box is saved in the centre of the goal. Assisted by Raheem Sterling.
Delay over. They are ready to continue.
Delay in match because of an injury Malo Gusto (Chelsea).
Attempt missed. Daniel Barlaser (Middlesbrough) right footed shot from outside the box is too high. Assisted by Hayden Hackney following a fast break.
Corner, Middlesbrough. Conceded by Malo Gusto.

2 years ago
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