The girl was just 13 years old and a virgin when her teacher had sex with her in 2003.
From then until 2007, they had many sexual encounters in rented cars, hotel rooms and even at the girl's home, where he rented a room.
The man, who has since been dismissed by the Ministry of Education, was jailed for 4½ years yesterday.
District Judge Siva Shanmugam noted that the man is 16 years older than the girl.
He said: "The accused had breached the trust reposed in him by the school, the girl and her mother.
"There was a high degree of exploitation as the teacher had committed penetrative acts on the minor.''
On Dec 9 last year, the former teacher, now 42, pleaded guilty to two counts each of having carnal connection with the underage girl, committing an obscene act on her and insulting a woman's modesty.
Thirty-six other charges were taken into consideration.
The man, who cannot be named due a gag order, was the girl's history and English teacher in 2003.
In June that year, he started courting her and got close to her by getting her to help mark papers, as she was in a group of students he was giving free tuition to.
He started having sex with her in November that year.
He also convinced her to be his girlfriend and bought her anything she wanted.
The court heard that he secretly filmed some of their trysts without the girl's knowledge.
In 2004, he rented a room from her mother, claiming that he needed a place to stay as he was undergoing divorce proceedings.
Twice, in 2006 and 2007, she tried to end the relationship, but he refused to let her go, until 2008. Yet, he continued living with the girl and her mother.
In mid-2009, as the girl was showering, she discovered his mobile phone, with its recording function on.
She told her mother, who asked him to move out.
But he begged her to let him stay, promising not do it again.
In July 2013, he was asked to move out as the girl's older brother was getting married and planned to move in with the family.
When the girl was checking to ensure that he did not take any of her belongings, she was shocked to discover more nude videos.
He had also secretly filmed her and her mother showering several times in 2010.
She made a police report and officers arrested him on Aug 23, 2013.
For each count of carnal connection, he could have been jailed up to five years and fined up to $10,000.
This article was first published on January 14, 2016.
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