Despite keen interest from S-League and regional football clubs, Irfan Fandi, 20, and his 18-year-old brother Ikhsan are set to try their luck in Europe next year after they complete their National Service in February.
The Straits Times (ST) understands that the sons of local icon Fandi Ahmad could attend trials with Leeds United in March.
Leeds are seventh in the Championship, the second tier of English football. The three-time English champions (1969, 1974 and 1992) are owned by Andrea Radrizzani, co-founder of MP & Silva and founder of Eleven Sports, both of which have offices here.
Irfan, who has 11 caps and one international goal, told ST: "I feel confident about showing what I'm capable of as a defender, which I feel I made a smooth conversion to from a forward.
"It's a form of recognition when a top Thai team like Bangkok Glass are interested to sign me. But my dream is to play in Europe."
With the exception of England-born Daniel Bennett, who played for Wrexham in the lower tiers in the 2001-02 and 2002-03 seasons, no Singaporean footballer has plied his trade in the English leagues.
It is not difficult to see why, as England has one of the strictest work permit rules in Europe.
Former Fifa intermediary and Singapore international R. Sasikumar told ST: "In the beginning, it will be almost impossible for our players like Irfan to sign for English clubs, and it is not because of the lack of ability.
"Players who want to play in England have to come from the top-50 national teams in the Fifa rankings. They also have to play a certain percentage of international games.
"And that's just one of many criteria. Those who don't satisfy these will be reviewed case by case."
Singapore's world ranking stands at No. 170 and Lions seeking a move to England will need to feature in at least 75 per cent of international fixtures - a criterion Irfan has met.
Sasikumar believes "there's still hope" for the likes of Irfan.
"If English clubs see value in a player, they can still place him in a feeder team in Belgium or Scandinavia and if he proves himself there, they have a better case to apply for a work permit in England," he explained.
Fandi is aware of the challenges and is exploring possibilities in other European leagues, like those in Scandinavia, to give his sons the best chance of making it abroad.
The national assistant coach, who will take charge of the Young Lions in the new S-League season, said: "Both Irfan and Ikhsan already have offers from clubs in the region, but we want to be fair to these teams and let them know they are trying to make it in Europe and could leave for trials any time from March to May. One plan is to sign them with the Young Lions so it would be easier for them to try out in Europe."