Mr Daron Tan and Mr Zachary Foo, both 22, scored top A-level grades and had their minds set on studying law.
They tried getting places at the top British universities, including Oxford, University College London and King's College.
Mr Foo also applied to the National University of Singapore (NUS) and Singapore Management University (SMU).
When they received an offer of a place from Oxford, both of them chose to go there.
Mr Tan, a former Raffles Institution student, decided not to apply to the local universities after receiving the offer from Oxford.
"I had always wanted to study overseas as I felt that I would get more out of being thrown into a different, challenging environment," he said.
He added that he felt "somewhat guilty" about his parents having to pay for his education at Oxford, which will come up to $200,000 over three years.
His father is an IT professional working in a bank and his mother is a housewife.
Having spent one year at Oxford, he feels that he has gained much from the experience.
Said Mr Tan: "You have two or three students to a tutor and you are forced to debate and defend your ideas. I have become a lot more confident of speaking up."
Mr Foo, a former student of St Andrew's Junior College, was offered a place to study law at both NUS and SMU.
He cited reasons similar to Mr Tan's for opting to go overseas. He said part of the attraction of reading law at Oxford for Singaporeans is the chance to work in the "magic circle" of elite law firms in London.
Now about to start his second year at Oxford, he has already gone for recruitment talks at top law firms in London and hopes to land an internship stint with one of them in his second year.
Mr Foo's studies are paid for by his mother, who works in a bank, and his father, a lecturer.
He said of his Oxford education so far: "It's interesting, it's multi- faceted. I feel I am getting a lot out of it."
Asked if they will return to Singapore, Mr Foo said he is likely to, but Mr Tan said he would like to explore work opportunities in London for a few years at least.
"From what my seniors tell me, you get to delve into different areas of law and cases that are multi-jurisdictional.
"That sounds interesting to me," said Mr Tan.