Major setback for Middlesbrough as a disappointing verdict is announced.

Middlesbrough have been dealt a major setback after it emerged that Tommy Conway will miss the Championship play-off final if the club are reinstated into the competition ahead of Southampton.

The striker suffered an ankle injury during Tuesday night’s second-leg defeat at St Mary’s and subsequent scans have confirmed the issue is serious enough to require surgery. The development means Conway faces a lengthy spell on the sidelines at one of the most important moments of both his club and international career.

Middlesbrough’s Tommy Conway (Image: Martin Rickett/PA Wire)

Conway went down late in the match after taking a heavy knock to his ankle and was unable to continue after receiving treatment from Middlesbrough’s medical team. The forward was substituted with 17 minutes remaining after clearly struggling with the problem.

Medical examinations carried out later in the week have now revealed significant damage, with surgery required to correct the issue. As a result, the 23-year-old will not be available even if Middlesbrough are handed a dramatic reprieve by the EFL’s Independent Disciplinary Commission.

The commission is expected to meet within the next 48 hours to determine whether Southampton breached regulations relating to alleged spying incidents before the play-off semi-final clash. Middlesbrough are hoping to be reinstated into the final against Hull City if disciplinary action is taken against Southampton.

However, even if Boro are granted a place at Wembley, Conway will play no part in the match due to the seriousness of his ankle injury.

That represents a massive blow for manager Kim Hellberg and his squad, considering Conway has been one of Middlesbrough’s most influential attacking players throughout the season.

The Scotland international has featured in every one of Middlesbrough’s 46 Championship matches this campaign and started 43 of those games. He also played in both legs of the play-off semi-final tie before being forced off injured at St Mary’s.

Conway initially operated as a central striker during the early part of the campaign, but in recent months he has been shifted into a role on the left side of the attack. That tactical adjustment proved highly effective for Middlesbrough, with the forward using his pace, movement and direct running ability to cause serious problems for opposition defences.

His ability to drift inside from the flank and attack goal-scoring areas became an increasingly important part of Middlesbrough’s system under Hellberg.

The attacker finished the regular season in outstanding form, scoring six goals in the final six league matches and helping drive Boro into the play-off positions. During that period, Conway also developed a strong understanding with fellow forward David Strelec, with the pair combining effectively in Middlesbrough’s frontline.

Now, Middlesbrough may have to prepare for a potential Wembley showdown without one of their key attacking threats.

If the club are reinstated into the final, Hellberg will need to identify a replacement solution on the left side of the attack. Several options are available to the Swedish coach, although none offer exactly the same qualities as Conway.

Leo Castledine, Sontje Hansen and Sammy Silvera are among the players capable of filling a wide attacking role.

Another possible option could involve moving Riley McGree into a more advanced attacking position. That scenario could become more realistic if midfielder Hayden Hackney is passed fit to return in time for a potential final appearance.

Hackney, who was recently recognised as the Championship Player of the Year, could slot back into central midfield and allow McGree to operate closer to the frontline.

Regardless of the tactical approach chosen, losing Conway at this stage of the season leaves Middlesbrough facing a difficult challenge.

The injury is also devastating news for Scotland national football team manager Steve Clarke ahead of this summer’s World Cup tournament.

Conway had been involved regularly during Scotland’s World Cup qualifying campaign and recently returned to the national team squad for the March international friendlies.

During those matches, he operated in the same wide attacking role he has been playing for Middlesbrough in recent months. His performances had reportedly placed him firmly in contention for a place in Scotland’s World Cup squad, which is due to be announced on Tuesday.

There had even been suggestions Conway could feature in Clarke’s starting line-up for Scotland’s opening group match against Haiti national football team on June 13.

Instead, the forward now faces a summer focused entirely on recovery and rehabilitation following surgery.

It is another cruel setback for Conway, who had worked hard to establish himself as both a key figure for Middlesbrough and an increasingly important option for the national team.

At this stage, there remains uncertainty surrounding the exact timeline for his recovery. Middlesbrough are still waiting to determine whether Conway will be fit to resume full training when the squad returns for pre-season preparations later this summer.

Medical staff are expected to assess his progress carefully following surgery before setting out a detailed rehabilitation programme.

For Middlesbrough, the timing of the injury could hardly be worse. The club are already facing uncertainty over the outcome of the ongoing disciplinary case involving Southampton, and now they must also consider the possibility of navigating a play-off final without one of their standout performers.

Conway’s energy, versatility and goal-scoring form made him one of the most important players in Middlesbrough’s late-season surge toward the play-offs.

His absence will not only weaken the team tactically, but also remove one of the squad’s most confident attacking outlets heading into what could become the biggest match of the season.

While Middlesbrough continue to wait for the outcome of the EFL disciplinary hearing, the club must now also prepare contingency plans without the services of Tommy Conway.

For the player himself, the focus shifts away from Wembley dreams and World Cup ambitions toward surgery, rehabilitation and ensuring he can return fully fit for the challenges ahead next season.