Mr Richmond Tan, 18, collected his A-level results at Pioneer Junior College (PJC) yesterday.
He is already planning his next step, looking up possible scholarships he can apply for.
Speaking to The New Paper before collecting his results, Mr Tan said: "I've been studying so hard, struggling so hard for the past 10 years just for this day."
It is one step closer to being able to work to support his family, he added.
The arts student scored an A and two Bs for his three H2 subjects, results he is "okay" with.
But PJC principal, Mrs Tan-Kek Lee Yong, said in a separate interview: "Many of us (in school) were so moved to tears, because we felt like the door is now open for (Richmond).
"He is getting closer to his goal of a place in university. He is not exactly your top student, but we all know how hard this boy has been working...
"Everyone, including the office clerk, loves him. He is a sweet, humble and polite boy."
Since he was young, Mr Tan and his brother Ryan, 17, have had to go through trying circumstances.
As toddlers, they watched their mother leave the family.
When he became a teenager, he watched his father struggle with a gambling addiction.
Eventually, the family had to give up their four-room flat in Sembawang due to financial difficulties.
They spent some time being homeless before finding lodging in another flat.
Mr Tan said he tried to help his father quit gambling by taking him to a rehabilitation centre for gambling addicts.
Three months later, his father dropped out, he added. But it was at the same centre that the teen met a volunteer, who later helped him earn his place in PJC.
Mr Tan had appealed to the school twice but was rejected. It was the third appeal with the volunteer that changed Mrs Tan's mind.
"(The volunteer) told me this boy's history. I was moved by his account of what Richmond has done. I realised I was not dealing with any ordinary student, but one who showed perseverance," said the principal.
She decided to allow him to study his choice of subjects even though he did not meet the criteria due to his poor English grade and subject combination.
Mrs Tan explained: "I told Richmond, 'I will bend all the rules to let you choose the subjects, but you have to show me that you put in effort'. I insisted he take on extra coaching for language and do a bit of bridging with my other teachers."
She added: "I was equally dragged into his passion after hearing about his circumstances. I wanted to make sure that if I gave this boy a chance, he really could manage. Otherwise, it is really poor decision-making on my part."
Over the two years, Mrs Tan and her teachers kept tabs on Mr Tan's well-being in school.
She asked for the teachers to pay extra attention to him and give him coaching.
She made sure he stopped waking up at 4am to study in case the long school hours tired him out.
She even made her civics tutor watch him finish up a bottle of chicken essence before breakfast as she was getting worried about his health.
"Otherwise he will give it to his grandfather," Mrs Tan explained, adding that he cares a lot for his 78-year-old grandfather, Mr Tan Khoon Seng.
The family now relies largely on the $1,300 the elderly man earns as a cleaner.
Mr Tan hopes he can soon work and earn enough for his grandfather to finally enjoy life in his golden years.
It has been five years since the teen assumed the role as the head of the family, and he has found the balance between his studies and making sure everyone is on the right track.
His younger brother, Ryan, for instance, was released from Boys' Home last month and is now studying in the Institute of Education.
As for his father, Mr Tan said they still quarrel often over money matters.
"But bo bian (Hokkien for no choice). Blood is thicker than water, I can't not care for him. He is my father.
"I still believe that one day he will change," he said.
This article was first published on March 5, 2016.
Get The New Paper for more stories.