Jonathan Woodgate's first taste of the Carabao Cup as a manager ended in a shock exit as Middlesbrough lost 4-2 on penalties against League Two side Crewe.
Boro were eventually made to pay for two disappointing goals in a poor first-half performance against David Artell's side, as boos rang out in a sparsely-occupied Riverside Stadium.
While Crewe scored all four of their spot-kicks on Teesside, Middlesbrough ended up losing after two awful penalties from Britt Assombalonga and Marcus Browne.
Middlesbrough, who have yet to win in two Championship games under Woodgate, had struggled to make inroads on the Crewe goal when they found themselves two down at the break.
Chris Porter had put the visitors ahead in the 41st minute, even if there was a hint of fortune about it. The striker turned in Olly Lancashire's effort from close range after some clever work from Charlie Kirk when a corner had not been dealt with.
And less than four minutes later Kirk was the scorer himself. This time he worked his way free in the Middlesbrough penalty area and was picked out by Owen Dale after the hosts had lost possession, again. Kirk found the inside of Aynsley Pears' far post.
Woodgate threw on Assombalonga and Paddy McNair for the second half and that was followed by the introduction of Ashley Fletcher.
Those changes had the desired effect as Fletcher curled Middlesbrough back into it with quarter of an hour remaining.
Then summer recruit from Blackpool Marc Bola marked his debut by hammering in a low equaliser in the first minute of stoppage-time to send the game to penalties – where Crewe would ultimately prevail.
