The 2027 AFC Asian Cup draw, held late Saturday in Riyadh, Saudi Arabia, has placed Singapore in a challenging Group D alongside former champions Australia and Iraq, as well as Tajikistan.
Singapore's matches are set for January 9, 14, and 19, 2027.
Defending champion Qatar was drawn into a tough group with Japan, Thailand, and Indonesia.
Tournament hosts Saudi Arabia, along with Japan, South Korea, and Australia-all bound for this summer's World Cup-are considered favorites to advance.
This marks Singapore's first qualification on merit. The Lions secured their spot in November 2025 by topping their qualifying group with a comeback 2-1 win over Hong Kong, followed by a 1-0 victory over Bangladesh in March.
Singapore's only prior Asian Cup appearance was in 1984, when they qualified automatically as hosts.
The draw was postponed from April 11 due to the conflict in the Middle East.
Currently ranked 147th in the world, Singapore is the lowest-ranked qualified team. Head coach Gavin Lee emphasized the importance of preparation, with friendlies against Mongolia on May 31 and China on June 5 at Jalan Besar Stadium.