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Tommy Conway’s World Cup Gamble: Why These Two Friendlies Define His Summer

Marcus Osei
Marcus Osei Senior Football Writer & Analyst
May 21, 2026
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Tommy Conway’s World Cup Gamble: Why These Two Friendlies Define His Summer
Photo: Editorial Research

Tommy Conway has been brutally honest. Miss this camp, miss the World Cup. That kind of clarity of thought either breaks a player or drives them. Everything points to it driving the Middlesbrough striker.

Three Missed Camps and a Denmark Night He Won’t Forget

Conway wasn’t part of Scotland’s qualification journey. He watched from the outside as his international teammates secured their place at the FIFA World Cup with that famous win over Denmark at Hampden. By his own admission, he started to wonder whether he had a future with the national side at all.

Those aren’t the words of a player coasting. They’re the words of someone who felt the ground shifting beneath him and decided to respond rather than sulk. Six caps in, with a gap that stretched back to a friendly against Liechtenstein in June, Conway had serious work to do to convince Steve Clarke he deserved a seat on the plane this summer.

Missing that Denmark night gave him what he calls ‘fire in the belly’. We believe him. Players who frame setbacks as motivation and then back it up with numbers tend to be the ones you want in a squad.

What His Championship Form Actually Tells Us

Eight goals in 39 Championship games won’t set the world alight on paper, but the context matters more than the raw numbers. Middlesbrough are sitting second in the table with seven games left, chasing a Premier League promotion spot, and Conway has been a consistent contributor to that push.

Playing in a high-stakes, physical division week after week is exactly the kind of test that sharpens a striker. He’s not operating in a system built around him. He’s earning his goals in a competitive, pressure-driven environment where games genuinely mean something. That’s the profile Scotland need at a World Cup, not a comfort-zone player but someone accustomed to delivering when the margin for error is thin.

The promotion battle at Middlesbrough and the Scotland squad race are running in parallel right now, and Conway is treating both with the same mentality. That’s a good sign.

Japan and Ivory Coast as Auditions

Saturday’s friendly against Japan at Hampden and Tuesday’s game against Ivory Coast at Everton’s Hill Dickinson Stadium are, on the surface, routine pre-tournament warmups. For Conway, they’re something closer to a job interview.

Scotland have options up front and Clarke will be weighing up his final squad with real care. Conway knows a strong showing across these two fixtures puts him in the conversation. A blank return and he’s back on the outside looking in.

From a betting perspective, Conway is worth watching closely in both games. If Clarke gives him meaningful minutes, he’s a player in form, hungry to prove a point, and playing with the kind of purpose that tends to produce results. Backing him to score in either fixture carries genuine logic, not just hope.

Ivory Coast present a different kind of test to Japan, more physical, more direct, and arguably the sharper challenge for a centre-forward trying to show he can handle international football at the highest level. If Conway can make an impact against them in particular, it sends a message that’s hard to ignore.

Read more: World Cup Play-Off Paths Ranked: Where the Value Lies and Who We Think Goes Through

Our Call on Whether He Makes the Plane

We think he makes it. Players who come back into squads after a spell out and immediately talk about using their absence as fuel, then follow through with consistent club form, tend to reward that trust. Clarke has always valued players who bring more than just technical ability. Work rate, mentality and a willingness to compete matter to him.

Conway ticks those boxes. He’s at a club fighting for promotion, he’s contributing goals in a demanding league, and he’s shown the self-awareness to understand exactly what was at stake when this Scotland call-up arrived.

The FIFA World Cup this summer will be the biggest stage Scottish football has graced in a generation. Conway wants to be part of it. After watching the Denmark celebrations from afar, we’d back him to do whatever it takes to make sure he’s in that squad when the names are read out.

Marcus Osei

Editorial Note: Marcus Osei

Senior football writer and tactical analyst with 12+ years covering the Premier League, Champions League, and world football. Born in Accra, raised between London and Kuala Lumpur.

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