It is less than a fortnight since Daniel Farke’s side won their euphoric opening game 1-0 against Everton, but that was followed five days later by a thumping 5-0 defeat at Arsenal.
And while that result was forgivable against the side that have finished second in the table for three seasons on the spin, Tuesday night’s debacle was somewhat concerning.
Leeds travelled to a near-empty Hillsborough for a League Cup second round tie against, Sheffield Wednesday, a club in total disarray.
Finnancial issues have ravaged the Owls for months, while outspoken owner Dejphon Chansiri is hugely unpopular among the fanbase.
Many fans are boycotting the ground at present, while a paper-thin squad has left the team desperately trying to be competitive.
Wednesday fielded a side that was largely akin to a youth team on Tuesday night, but they took a shock lead when Karl Darlow spilled Jamal Lowe’s cross-shot through his legs for an own goal.
To put the Owls’ team into context, Lowe was their only outfield starter to have made than 18 professional appearances in football.
Leeds eventually equalised through Jayden Bogle, but otherwise they could not find a way past inspired new home keeper Ethan Horvath.
And that proved to be the case in the penalty shootout, as the American produced extraordinary heroics.
He saved two of Leeds’ spot-kicks, from Joel Piroe and Sean Longstaff, while Dominic Calvert-Lewin, who had missed a couple of great chances late on, spooned his effort over the crossbar.
Conversely, the Owls were perfect from the spot, wining the shootout 3-0 to set up a third-round tie at home to League Two Grimsby.
The Mariners, whose side featured former Bantams Charles Vernam and Reece Staunton, as well as current City player Clarke Oduor on loan, made it through with an astonishing win over Manchester United.
Charles Vernam, who scored 10 goals in 54 appearances for the Bantams, thundered home Grimsby's opener in their astonishing win over Manchester United on Wednesday night.Charles Vernam, who scored 10 goals in 54 appearances for the Bantams, thundered home Grimsby's opener in their astonishing win over Manchester United on Wednesday night. (Image: Nigel French/PA Wire)
The sides drew 2-2 at Blundell Park on Wednesday night, United scoring twice late on to take the game to penalties.
But Grimsby held their nerve, winning a remarkable shootout 12-11 to knock out the Premier League giants and six-time winners of the tournament.