THIS is what happens when things just aren’t going your way. A Carabao Cup first-round exit might not be a disaster, even when it comes at the hands of opponents who are a division below you, but the concession of a stoppage-time strike at the Riverside last night pretty much sums things up for Middlesbrough at the moment. On and off the pitch, this has not been a good start to the season.

While the capture of Matthew Hoppe should help address some of Boro’s attacking shortcomings, with the American having been paraded on the pitch before kick-off following his arrival from Mallorca on a four-year deal, the Teessiders still need to make another three or four additions before the transfer window closes at the end of the month.

Results so far this season underline that, with last night’s defeat meaning Chris Wilder’s side are still searching for their opening win of the campaign after three games without a victory. Fail to beat Sheffield United on Sunday, and the alarm bells really will be ringing.

Last night’s defeat came in a game that saw Wilder make eight changes to his starting side, and was somewhat undeserved given that Boro dominated possession and territory for most of the evening.

Duncan Watmore missed a golden early opportunity, while Dael Fry saw a second-half effort well saved, but for all their control of much of the game, the Teessiders struggled to carve out clear opportunities.

As a result, they were always vulnerable to the sucker-punch that arrived in stoppage time, with Barnsley substitute Josh Benson slotting home the rebound after his initial effort had been parried by Boro goalkeeper Liam Roberts. With penalties looming, the Teessiders were beaten before they could even step up from 12 yards.

The first round of the Carabao Cup tends to offer managers an opportunity to experiment, so it was no surprise to see Wilder adopting a mix-and-match approach to his starting line-up.

There was experience at the back in the shape of Paddy McNair and Fry, who were both making their first starts of the season in front of debutant goalkeeper Roberts, who signed earlier this summer from Northampton Town.

Youth was the order of the day further up the field though, with fledgling midfielders Hayden Hackney and Joe Gibson supporting attacking debutant Sonny Finch. Finch, who hails from Houghton-le-Spring, only turned 17 at the start of the month, but having recently signed his first professional contract, he is clearly regarded as a potential breakthrough star. With Josh Coburn sidelined through injury, it will be interesting to see if he is retained as part of the first-team squad in the next few weeks or sent out on loan.

Finch was bright and industrious without ever really looking like scoring, a description that could also be applied to his strike partner, Watmore. There is plenty that is positive about Watmore’s game, not least his refusal to give up on seemingly lost causes and his willingness to close down opposition centre-halves, but he has always suffered from a lack of composure in front of goal. Sure enough, that failing was glaringly apparent within the opening two minutes of last night’s game.

Having been sent clear of the Barnsley defence, Watmore was one-on-one with Barnsley goalkeeper Jack Walton as he bore down on goal. A clinical finish into either corner would have opened the scoring, but instead, Watmore’s side-footed effort was directed much too close to Walton, who was able to save with his right boot. Having missed an even easier chance against West Brom on the opening day of the season, Watmore is hardly persuading Wilder that he is the answer to Boro’s goalscoring issues.

Boro’s bright start also saw Hackney fizz a 20-yard effort just wide, but as the first half wore on, so it was Barnsley that began to offer more of a threat despite their League One status.

Luca Connell curled a free-kick over the crossbar before centre-half Mads Andersen fired in a long-range strike that Roberts did well to parry. Boro’s stand-in shot-stopper did even better on the half-hour mark, blocking Aiden Marsh’s close-range effort after the Barnsley forward wriggled free on the edge of the six-yard box.

With Jack Aitchison firing a first-time effort just wide on the stroke of half-time, Boro ended the first half being pegged back, but they gradually regained the initiative at the start of the second period, with Gibson firing a shot wide of the upright after a slick interchange of passes with Tommy Smith.

McNair should probably have done better when he glanced a header wide from a corner just before the hour mark, with the miss proving to be one of his final contributions before he was taken off as part of a triple-change that also saw Watmore and Finch depart from Marcus Forss and Chuba Akpom.

Akpom’s arrival, in particular, provided a focal point for Boro’s attacking, although a combination of some sloppy approach play and some resolute Barnsley defending meant chances remained few and far between in the closing stages.

Forss almost broke through with quarter-of-an-hour remaining, after Fry strode purposefully out of defence, but the Finn was unable to shake off the attention of two Barnsley defenders. The hosts’ best late opportunity came with eight minutes remaining, but while Fry found the target with a header from Caolan Boyd-Munce’s cross, Walton tipped the ball over.

That looked like being that, but with penalties looming, Benson struck. Roberts should probably have done better with the substitute’s initial effort, and the Barnsley midfielder reacted quicker than any of Boro’s defenders to pounce on the rebound.