Tampines Rovers will face Indian champions Bengaluru in the AFC Cup quarter-finals.
The quarter-finals will be a two-legged affair, with the winners of the tie meeting either reigning champions Johor Darul Ta'zim or Hong Kong's South China as the rules have changed this year and only allowed East Asian teams to play each other until the semi-finals.
The first leg will be played in India, September 14 and the return leg will fall on September 21.
The last time a Singapore team reached the AFC Cup semi-finals was in 2004, when both Geylang International (known as Geylang United then) and Home United were in the final four.
Tampines have never advanced past the quarter-finals.
Air Force Club (IRQ) vs Al Jaish (SYR)
Al Ahed FC (LIB) vs Al Muharraq (BHR)
South China (HKG) vs Johor Darul Ta'zim (MAS)
Bengalaru (IND) vs Tampines Rovers (SIN)