Chelsea striker Cole Palmer squandered a hat-trick of chances as Hayden Hackney handed Sky Bet Championship Middlesbrough a priceless first-leg lead in their Carabao Cup semi-final.

The England international, who had earlier been denied by Boro keeper Tom Glover, passed up three opportunities either side of Hackney’s 37th-minute strike, which ensured Michael Carrick’s men will head for Stamford Bridge in a fortnight’s time with a 1-0 lead.

On a night when the 2004 winners managed to frustrate the side who beat them in the 1998 final for long periods, the big-spending Premier League club failed to find top gear despite boss Mauricio Pochettino naming Thiago Silva, Levi Colwill, Enzo Fernandez, Moises Caicedo, Conor Gallagher, Raheem Sterling and Palmer in a strong starting line-up.

For their part, the Teessiders were organised, dogged and a threat on the break, and reaped the rewards three days after suffering a heartbreaking late defeat by top-flight Aston Villa in the FA Cup.

The visitors’ goal came under threat within seconds of kick-off when Colwill’s poorly-directed header delivered the ball straight into the path of Emmanuel Latte Lath, although the striker scuffed his shot straight at keeper Djordje Petrovic as defender Axel Disasi tried desperately to close him down and caught him in his follow-through.

The Boro frontman struggled on after treatment, but eventually limped off to be replaced by Josh Coburn with just five minutes gone.

Palmer forced Glover into a full-length save as Chelsea responded, but with widemen Isaiah Jones and Alex Bangura – whose evening was ended prematurely minutes later by a hamstring injury – enjoying the space afforded to them, the Teessiders made early inroads.

The occasional flurry from Noni Madueke aside, neither team was able to create a chance of note until Colwill headed over from Palmer’s 29th-minute cross, but Jonny Howson was fortunate to get away with a dreadful crossfield pass which put Palmer in on goal two minutes later, only for the 21-year-old to drag his shot wastefully wide.

Chelsea were made to pay with eight minutes of the first half remaining when Dan Barlaser played Jones in behind Colwill and he crossed to Hackney at the near post to stab past Petrovic.

Palmer had two glorious opportunities to level in stoppage time when he spooned the ball over the top after Glover had spilled Enzo Fernandez’s shot from distance, and then failed to beat the keeper after cutting inside from the right.

The visitors remained patient on their return but largely played in front of Boro, who looked comfortable in their shape as they protected a precious advantage with little fuss.

Madueke headed straight at Glover from Fernandez’s 53rd-minute cross and then flashed the ball dangerously across goal after worming his way in from the right, and Gallagher fired wide on the turn eight minutes later amid relentless pressure.

Mykhailo Mudryk and Armando Broja were introduced with little sign of an equaliser imminent and after Barlaser had shot high and wide from a pacy counter-attack, Glover needed two attempts to collect Mudryk’s 73rd-minute attempt.

However, that was as good as it got for Pochettino’s misfiring side, who have work to do on home soil in the deciding leg.