Singapore draw Japan in Group E
The three teams will be joined by Afghanistan and Cambodia in Group E, with all teams set to play each other in a home-and-away round-robin format.
Southeast Asian neighbours Cambodia are Singapore's first opponents, with the Lions visiting on 11 June to kick things off.
Singapore's first home game will be against Japan on 16 June, with the Samurai Blue set to return after facing Brazil in a glamour friendly at the National Stadium just last year.
The Lions will also have good memories of playing against Syria after beating them at home during the Asian Cup qualifiers in 2013, although the Syrians got their revenge in the return fixture.
Afghanistan are the one wildcard, with Singapore never having played them before.
Meanwhile, archrivals Malaysia have been drawn in Group A together with the UAE, Saudi Arabia, Palestine and Timor-Leste, while there is a mini-Southeast Asian reunion in Group F with Vietnam, Thailand and Indonesia being joined by Iraq and Chinese Taipei.
Asian Cup champions Australia head up a fairly straightforward Group B, where their biggest challengers will likely be Jordan.
Eight group winners and the four best group runners-up will advance to the third round of World Cup qualification, as well as qualify for the 2019 Asian Cup finals.
The remaining four group runners-up will be joined the four best fourth-placed teams in the Asian Cup qualifying third round, with the remaining fourth-placed teams entering the Asian Cup qualifying playoffs.