Chelsea have seen their fair share of interim bosses over the years, but the number of caretakers who have actually gone on to win major trophies remains surprisingly small.

Calum McFarlane now has the opportunity to achieve something quite uncommon this Saturday afternoon.

If he can guide Chelsea to victory over Manchester City in the FA Cup final, McFarlane would join an exclusive list of managers who have claimed major honours while serving as caretakers for either club or country.

Here are some notable examples from football history — and a recurring theme may become apparent rather quickly.

This first case stretches the definition of a ‘caretaker manager’ somewhat, as some accounts describe him more as a short-term appointee later made permanent, rather than an official interim boss.

Still, it fits the spirit of the role. Mario Zagallo, who had already won the World Cup as a player in 1958 and 1962, took charge of Brazil just 75 days before their 1970 World Cup campaign began, following the dismissal of João Saldanha.

Zagallo brought back Pelé to the national team setup, and the duo led Brazil to an unforgettable triumph, defeating Italy 4–1 in the final with one of the most iconic performances in football history. His success earned him a longer spell as Brazil’s full-time manager.

Now to the start of what became something of a pattern at Chelsea.

After Avram Grant had taken Chelsea to the Champions League final in 2008 following José Mourinho’s departure, he too was dismissed. Luiz Felipe Scolari was brought in but lasted only a short while before being replaced by Guus Hiddink as a temporary solution, likely while the club awaited Carlo Ancelotti’s availability at AC Milan.

Hiddink quickly won over the Chelsea faithful, losing just one of his 22 games in charge and winning 16.

His final victory came in the 2009 FA Cup final, where Chelsea recovered from Louis Saha’s record-breaking fastest goal in a final to defeat Everton 2–1.

Fast forward three years, and Chelsea found themselves repeating history.

Andre Villas-Boas struggled to make his mark at Stamford Bridge and was replaced by former Blues midfielder Roberto Di Matteo, who had previously managed MK Dons and West Bromwich Albion before returning as Villas-Boas’ assistant.

At the time, Chelsea faced a 3–1 deficit against Napoli in the Champions League Round of 16, but under Di Matteo, they turned it around with a 4–1 second-leg victory to progress. The team then went on to defeat Benfica, Barcelona, and finally Bayern Munich to secure Chelsea’s first-ever Champions League trophy.

In addition, during his interim spell, Di Matteo also guided Chelsea to the FA Cup title with a 2–1 win over Liverpool. And speaking of Liverpool and Chelsea, the connection didn’t end there.

Following Di Matteo’s achievements, Chelsea appointed him full-time — but he was dismissed before the end of November. The club then made a controversial move by bringing in former Liverpool manager Rafa Benitez as interim boss, a title he retained despite his objections throughout the 2012/13 season.

After facing heavy criticism from supporters early on, Benitez eventually earned grudging respect by guiding Chelsea to the Europa League crown and securing a third-place finish in the Premier League, ensuring a return to the Champions League.

There’s also the case of managers who started as caretakers and later won trophies after being made permanent.

Tony Barton stepped up as caretaker for Aston Villa in 1982 following Ron Saunders’ sudden resignation. Four months later, Barton led Villa to a famous European Cup victory over Bayern Munich.

Leanne Ross enjoyed a remarkable start to life as caretaker of Glasgow City, winning ten of her first eleven matches to put the club six points clear atop the Scottish Women’s Premier League in the 2022/23 season, later sealing the title soon after her permanent appointment.

And finally, Renee Slegers led Arsenal Women to the Women’s Champions League title last year after stepping in for Jonas Eidevall early in the season. During her caretaker spell, she guided the team to the quarter-finals and maintained an impressive 11-match unbeaten run.