Middlesbrough 2 Crewe 2 (Crewe win 4-2 on penalties)

THIS was an early learning experience for Middlesbrough’s rookie boss Jonathan Woodgate, a night when he was a picture of frustration in his technical area as his youthful team never looked in control against lower league opposition and paid the price.

Even when Boro finally responded to his calls to come from two goals down to snatch a draw in the dying seconds, it was Crewe Alexandra of League Two who still deservedly got to celebrate in the end after winning a penalty shoot-out.

Woodgate turned away and headed for the tunnel, with a backdrop of a few boos as well as applause from more respectful supporters, but he will share the frustrations of watching Middlesbrough bow out of the Carabao Cup at the first attempt under his guidance.

Make no mistake he wanted to progress, despite making the ten changes to the side that started the Championship game against Brentford. His extensive tinkering should have provided an opportunity for those given a chance to stake a claim for a league start, he is likely to have learned something from this though.

Instead this defeat and performance provided something of a reminder of how thin this Middlesbrough squad is, and that was clear by the time the half-time whistle was blown.

Crewe, who had looked dangerous throughout the first half, had edged two goals in front in the final four minutes of the first half. Chris Porter and Charlie Kirk ensured the visitors made the most of the gaps in the Middlesbrough backline to take control.

That led to boos and jeers from the small home support, as Woodgate held his cheeks in frustration, and there was more of that after the restart when striker Rudy Gestede was singled out for criticism after an ineffective night saw him replaced by Ashley Fletcher on the hour.

Quarter of an hour later Fletcher responded with a sweet goal to put Middlesbrough back into it and then summer signing Marc Bola, who had disappointed himself in the opening period, made amends with a late leveller to send the game to penalties.

Crewe still had the extra quality from 12 yards to get the job done.

While every one of their takers beat Aynsley Pears, Middlesbrough were left to rue another missed penalty from Assombalonga (missing the target) and Marcus Browne’s weak effort was held by goalkeeper Dave Richards.

That was that and there will not be many complaints emanating from Teesside this morning.

Woodgate might have been desperate for his first win in a competitive game but that didn’t stop him from making wholesale changes. He could well regret that this morning, with only midfielder Adam Clayton surviving from those who started against Brentford.

Among the five new starters were summer recruits Anfernee Dijksteel, Browne and Bola, while academy duo Pears and Ste Walker got the chance. It never went to plan.

It was Walker who forced goalkeeper Dave Richards into a low save. The young striker, highly-rated and back involved after spending half of last season on loan at MK Dons, created space for himself before getting his shot away to provide a sign of promise.

That was about as good as it got for Middlesbrough in the opening half.

Crewe had a better chance than that seconds later. Harry Pickering’s deep free-kick to the back post ended with Dale evading his marker but he headed over from inside six yards albeit from a difficult angle.

The Railwaymen looked to attack under manager David Artell and they were not afraid to put the home team under pressure. Middlesbrough looked unfazed at the back, or at least that was how it seemed, with Nathan Wood, George Friend and Pears seeing plenty of the ball as they looked to pass the ball between themselves.

There needed to be greater urgency in the attacking third. There were too many sloppy passes in that area, which was greeted by groans and moans from those supporters who turned up to watch. Worse was to come.

Middlesbrough didn’t have composure in an attacking sense. It was not until half an hour in that the men wearing red showed a hint of threat. There had a been a few half chances when Gestede headed over a Browne corner from six yards.

Crewe still looked more intent to make an impression and a sign of their growing confidence was when right-back Perry Ng worked his way deep into the Middlesbrough half, played a one-two on the edge of the area and then floated an effort wide.

It came as no surprise when they did find the breakthrough. A failure to deal with a corner properly ended with Crewe doing everything they could to get the ball back into the danger area, and their opponents doing the opposite.

Dale’s clever little run tormented the defence initially and after he rolled his pass into the area, Olly Lancashire was there to turn an effort towards goal where Porter was on hand to turn in even if he knew very little about it.

That led to a disappointing Middlesbrough first half performance being even poorer because they were even more wasteful in possession. When they lost the ball again four minutes later, Crewe countered and made the most of loads of space to add the second.

Kirk was the man allowed the freedom deep in the Middlesbrough half to run and roll a pass to Dale to do the rest, coolly finding the inside of Pears’ far corner to spark a chorus of boos and jeers from the home crowd that continued when the half-time whistle was blown.

Woodgate said his bit in the dressing room. He had his players back on the pitch with five minutes remaining of the allotted quarter of an hour for half-time, with Assombalonga and Paddy McNair tasked with turning the game around.

There was a bit more urgency in Middlesbrough’s play but, after Callum Ainley had been the only player to have an effort towards either goal, very little changed, so Gestede was replaced by Fletcher on the hour – and the Benin international trudged off the pitch hearing exactly what sections of the home support thought of his display.

That finally had the desired effect. After McNair had curled a low effort inches wide after a clever exchange with Assombalonga, Fletcher pulled Middlesbrough back into it with a similarly low finish that curled just inside Richards’ bottom right hand corner.

Just when it seemed Middlesbrough would not be able to find the crucial second goal, Bola was the surprise scored to level things up to force the game to penalties.

When a ball across the area evaded everyone, it rolled away from goal where Bola was on hand to hammer low and into the net. Despite the shortlived celebrations, that still wasn’t enough.