SINGAPORE – Lions head coach Gavin Lee was midway through his first year at Pasir Ris Secondary School when Carlo Ancelotti lifted his first UEFA Champions League title as a coach in 2003.

Next week, the pair will shake hands on the sidelines at the National Stadium, maybe share a cordial exchange, before taking their seats on the respective benches when Singapore host Brazil in an international friendly on Nov 17 as part of the Mizuho Blue Challenge – The Kallang Football Series Singapore.

The rare opportunity to go head-to-head with one of world football’s most successful and respected coaches is not lost on Lee, 36, even though he admitted he had not spent much time thinking about the coming encounter.

“Now that you’ve (said it), going up against Ancelotti... it’s like a player, right? When you get to go up against someone you see on TV, it can get quite surreal,” he said.

“But me and the boys are so zoomed in into what we do and what’s within our control, and so sometimes you don’t think so much about that. We are preparing against Paraguay and Brazil just like how we normally do against every other team.

“We don’t take things for granted, and we’re just trying to find ways to hurt them and try to prevent them from hurting us too much.

“But definitely, I think I’ll probably promise myself to take a moment to appreciate that situation before kick-off.”

Since winning that first Champions League with AC Milan , 67-year-old Ancelotti – who was appointed Brazil coach in May 2025 – has gone on to win a further four European Cups, as well as domestic league titles in France, England, Spain and Germany with the continent’s top clubs .

In Singapore this week, he will lead the world No.6 Selecao against 17th-ranked Japan in a rematch of their World Cup last-32 clash on Nov 14, and then Singapore three days later.

Singapore, meanwhile, will play world No.33 side Paraguay to open the quadrangular series on Nov 13 before playing Brazil.

Japan and Paraguay play each other to close off the series on Nov 17, after the Singapore-Brazil game.

When the world No. 149 Lions play Paraguay, Lee will be across the dugout from another veteran tactician in 64-year-old Argentine coach Gustavo Alfaro. Alfaro previously managed Argentine giants Boca Juniors and led Paraguay at the recent World Cup, where they knocked out Germany to progress to the Round of 16.

The daunting challenge posed by the South American sides is something Lee had always wanted for his charges as they prepare for an historic Asian Cup campaign in 2027.

The Lions, who have qualified for the continental competition for the first time, were drawn with heavyweights Australia and Iraq – who both featured at the World Cup in North America in July – and Tajikistan in Group D.

However the tournament, originally scheduled for January, has been postponed to December next year due to ongoing security concerns in Saudi Arabia, though this has not changed Lee’s outlook for the games .

Calling them a “very important step”, he added: “It’s not just to check a box of playing a strong team, right? Because in this kind of games, we expect ourselves to be overloaded, to be pushed, and it allows us to see what of our football survives and what needs to be better.”

Yet the rescheduling of the Asian Cup has also inevitably meant adjustments have had to be made, including to Lee’s own situation.

He had taken over the reins of the Singapore team from Japanese coach Tsutomu Oguara on an interim basis in June 2025, and, after guiding the side to a 2-1 win in Hong Kong five months later that sealed qualification for the Asian Cup, was appointed as Lions coach on a permanent basis till mid-2027.

With the tournament rescheduled to the year’s end, The Straits Times understands that the Football Association of Singapore has moved to extend Lee’s contract.

When asked about the contract extension, Lee said: “We had a discussion (and) I think an official announcement we made in due time. It is natural because we started a project together in that sense, and definitely, if given a chance, we want to see the project through.”

The postponement has also reinvigorated some players in Lee’s 24-man squad, who aim to make their case for a place on the plane to Saudi Arabia next year .

Geylang International captain and defender Joshua Pereira, whose last appearance in a Singapore shirt came in March 2023, admitted that he had expected not to make the squad if the tournament had taken place in January.

But with Geylang surprise leaders of the Singapore Premier League after six games, the 29-year-old has earned a recall and wants to make the most of this opportunity.

“I just keep working, put in consistent performances, and then hopefully it’ll be enough to stake a claim,” he said.

Creative Young Lions midfielder Joel Chew, 26, who only made substitute appearances during the Lions’ underwhelming FIFA Asean Cup campaign in September, is another who is geed up to impress.

“Getting as much playing time as possible, and just doing what I love while I still can, to the best of my abilities is what I prioritise the most now,” said Chew, who is looking forward to facing Ipswich Town attacker Julio Enciso against Paraguay.

“I’m just going to do what I can and do my best, and eventually, hopefully, that will be enough to be called up to the Asian Cup and hopefully, I will be gunning for a place in the first XI.”