Scotland is poised to set an unwelcome record if they lose to Portugal next week, which would mark their longest losing streak in the nation's 152-year history.
Following their latest setback against Croatia in Zagreb, Steve Clarke's win rate as Scotland manager has dropped below that of both Craig Levein and Alex McLeish during his second spell in charge.
The national team has managed to secure just one victory in their last 15 matches, and they now face Portugal at Hampden Park, hoping to avoid a fourth consecutive defeat in the UEFA Nations League and a total of five losses overall.
Historically, Scotland has never endured five straight defeats, making this upcoming clash critical, not just for Clarke's future in the role but for the country's pride.
As Scotland gears up to welcome Cristiano Ronaldo's Portugal on Tuesday, they find themselves in a challenging position, marked by a history that includes numerous struggles and 'what if' moments.
The Scots have faced significant adversity in the past, having suffered four consecutive defeats on five different occasions throughout their footballing journey.
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The first instance dates back to 1965, when Scotland fell to a formidable lineup that included Italy, England, the Netherlands, and Portugal.
Just eight years later, in 1973, the team faced another tough stretch, losing to Northern Ireland, England, Switzerland, and Brazil, showcasing the competitive nature of international football during that era.
Fast forward to the early 2000s, and Scotland's woes continued. In 2002, they endured a disappointing run against France, Nigeria, South Korea, and South Africa.
The following year saw a similar fate, as they were bested by the Netherlands, Wales, Romania, and Denmark in a string of matches that left fans disheartened.
The most recent occurrence of four consecutive losses came in 2019, when Scotland faced defeats against Belgium and Russia twice.
However, they managed to break this streak with a commanding 6-0 victory over San Marino shortly thereafter, providing a glimmer of hope.