Join The Club
Calum McFarlane has the chance to do something relatively rare on Saturday afternoon.
If he can mastermind a victory over Manchester City in the FA Cup final, Chelsea caretaker boss would join a short list of managers to have lifted major trophies while in interim charge of a club or a national side.
Mario Zagallo (Brazil, 1970)
This one requires a slightly squishy definition of 'caretaker manager', we have to admit, with some sources suggesting he was more a short-term appointment whose spell was later extended than being outright defined as an interim boss.
But we're going to go ahead and regard that as a technicality; it's certainly in the spirit of the caretaker boss.
What is clear is that Zagallo, who won the World Cup as a player in both 1958 and 1962, was appointed just 75 days before their 1970 World Cup campaign got under way following the difficult Joao Saldanha's dismissal.
Zagallo brought Pele back into the fold, and the former teammates went on to win the whole thing, beating Italy 4-1 in the final with an iconic performance. Zagallo got the job for a longer spell after the tournament.
Guus Hiddink (Chelsea, 2009)
The beginning of something of a tradition for Chelsea.
Avram Grant had taken Chelsea to the Champions League final the previous year after taking over from Jose Mourinho, only to get the chop himself. In came Luiz Felipe Scolari, who proved even more short-lived in the role.
Chelsea then turned to Guus Hiddink largely as a time-buying measure, presumably waiting for Carlo Ancelotti to see out his time at AC Milan.
But the Dutchman endeared himself to Chelsea fans by losing just one of his 22 games in charge, winning 16.
The last of those victories came in the 2009 FA Cup final, where Chelsea overcame Louis Saha's fastest-ever goal in a final to beat Everton 2-1.
Roberto Di Matteo (Chelsea, 2012)
Three years later, Chelsea were at it again.
Andre Villas-Boas had failed to assert himself at Stamford Bridge and was replaced by former Blues midfielder Roberto Di Matteo, who had previously managed MK Dons and West Brom before returning to the club as Villas-Boas' assistant.
Chelsea held a 3-1 first-leg deficit to Napoli in the Champions League last at the time, but Di Matteo took them to a 4-1 win in the second leg to put them through. They subsequently saw off Benfica, Barcelona, and finally Bayern Munich to deliver Chelsea's first-ever Champions League title.
But that wasn't all: in the interim (no pun intended), Di Matteo had also lifted the FA Cup thanks to a 2-1 victory over Liverpool. And speaking of Liverpool and Chelsea...
Rafael Benitez (Chelsea, 2013)
Yep, yet another one for Chelsea.
Di Matteo got the job full-time after helping Chelsea to their two trophies, but was gone before the end of November.
In his place, the club made the deeply unpopular decision to appoint former Reds boss Rafa Benitez as interim manager - a title he kept (despite his protests) for the rest of the 2012/13 campaign.
After months of protests, Benitez earned at least some begrudging respect by the end, leading Chelsea to win the Europa League title, as well as earning Champions League qualification by finishing third.
Honourable mentions - Tony Barton (Aston Villa, 1982), Leanne Ross (Glasgow City, 2023), Renee Slegers (Arsenal, 2025)
A trio here of managers who won trophies in seasons in which they had significant caretaker spells, but who had all been given the job permanently before they got their hands on their silverware.
Tony Barton stepped up from assistant manager with reigning English champions Aston Villa in 1982 following Ron Saunder's surprise resignation, initially on a caretaker basis. Four months later led Villa to a European Cup final victory over Bayern Munich.
Leanne Ross won ten of her first 11 games in charge of Glasgow City to send Glasgow City six points clear at the top of the Scottish Women's Premier League in 2022/23, and clinched the title a few weeks after being handed the job permanently.
And then there's Renee Slegers, who just last year led Arsenal to their Women's Champions League triumph having stepped up to succeed Jonas Eidevall early in the season and taken Arsenal to the quarter-finals during her caretaker spell as part of an 11-game unbeaten spell.
