Singapore were drawn against tournament favourites Thailand, Philippines and Indonesia in Group A of the AFF Suzuki Cup on Tuesday night.
It will likely not be the draw head coach V.Sundramoorthy was hoping for, starting with Thailand, who are the region's top dogs, ranked 121st in the world by FIFA, soon to commence the final round of World Cup qualifying and the reigning Suzuki Cup champions.
Philippines are ranked second within Southeast Asia at No.135 and as hosts they will have home ground advantage as well as the bulk of the support.
Indonesia are an unknown quantity, having only recently had their ban from international football overturned by FIFA, meaning they were unseeded in Tuesday night's draw.
But the Indonesian's will still possess plenty of talent and will likely prove another stern test for the Lions.
In Group B, co-host nation Myanmar will take on Malaysia, Vietnam and the winners of the final qualifying place, which is between Cambodia, Timor Leste, Laos and Brunei.