The Whites are coming into this match following a pulsating start to their Championship campaign, whilst Boro are looking to maintain their 100% record in competitive matches so far this season.
Match preview
Although they did not collect the win they strived for on the opening weekend of the Championship season, Leeds gave their supporters the opportunity to forget about May's playoff final defeat to Southampton by viewing a truly bizarre six-goal thriller against newly-promoted Portsmouth at Elland Road.
Despite dominating the possession and attacking metrics, Daniel Farke's troops found themselves fighting to steal a point after Callum Lang held his nerve from 12 yards out to fire Pompey into a late lead, before returning star Brenden Aaronson arrived off the bench to bag a 95th-minute equaliser for the hosts.
The Whites certainly missed the clinical edge provided so often last season by flying Dutchman Crysencio Summerville, who won Leeds' Golden Boot race in the 2023-24 term with 19 Championship strikes, earning himself a lucrative move to Premier League outfit West Ham United.
Regardless of their defensive frailties on the weekend, Farke's side will be relatively confident of advancing into the second round of the EFL Cup considering their excellent record at Elland Road, with Wednesday's hosts losing just twice at their Yorkshire base in the Championship last campaign.
One-time winners of this competition, Leeds squeezed past the attentions of Shrewsbury Town in the first round last season before becoming a shock second-round casualty on August 29, when the Championship powerhouses exited the competition at the home of League Two side Salford City following penalty kicks.
After an eighth-placed finish during the 2023-24 Championship season - finishing four points behind Norwich City in sixth - Middlesbrough commenced their push for a playoff spot this time around on a positive note, beating Luke Williams's Swansea City at the Riverside Stadium.
Making the goalscoring antics of Chuba Akpom on Teesside an increasingly-distant memory, Emmanuel Latte Lath kept his cool from the penalty spot in the first half of the contest to get the better of Lawrence Vigouroux in the visitors' net, securing all three points for Boro on the opening weekend.
Although a midweek trip to Elland Road is a daunting task at the best of times, Michael Carrick's charges will take confidence from their respectable away record in the Championship last season when they lost eight games on the road, with only the promoted trio of Leicester City (6), Ipswich Town (5) and Southampton (6) suffering fewer defeats on their respective travels.
Middlesbrough were the beneficiaries of some favourable early-round draws during last season's EFL Cup, however Wednesday's visitors still had to do the business against Huddersfield Town, Bolton Wanderers, Bradford City, Exeter City and Port Vale to earn a glamorous semi-final clash with Chelsea.
Beating the aforementioned Wanderers in the 2004 final at the Millenium Stadium in Cardiff, one-time winners Boro will strive to be the best-performing EFL side in the competition for a second straight year, a mission that begins with the challenge of promotion-chasing Leeds on Wednesday night.
Leeds United form (all competitions):
Middlesbrough form (all competitions):
Team News
As is often the case in the first round of the EFL Cup, Leeds could make a raft of changes to their Championship XI from the weekend, meaning that key starters such as Ethan Ampadu and Joe Rodon could drop out of the side.
Mateo Joseph was handed his maiden league start for the Whites on the weekend, although the Spaniard should be replaced by either Joel Piroe or Patrick Bamford on Wednesday night.
On loan from Bournemouth, goalscoring midfielder Joe Rothwell could make his full debut for Leeds, whilst youngsters Charlie Crew and Joe Gelhardt will be hoping to receive match minutes.
Middlesbrough right-back Luke Ayling could face off against his former employers at Elland Road, should Carrick opt to stick with the 32-year-old veteran.
There could be a first competitive start in Boro colours for Delano Burgzorg, who has experience in the EFL following his loan stint at Huddersfield Town last term.
Leeds United possible starting lineup:
Darlow; Bogle, Wober, Struijk, Byram; Rothwell, Crew, James, Aaronson, Piroe; Bamford
Middlesbrough possible starting lineup:
Glover; Ayling, Clarke, Van den Berg, Engel; Howson, Barlaser, Burgzorg, Morris, Azaz; Coburn
We say: Leeds United 3-1 Middlesbrough
Leeds are likely to make a host of alterations to their XI for Wednesday night, however they should still have enough quality on the pitch to cause Middlesbrough serious issues.