To many, she was "the beauty with the brains".
Ms Cheryl Marie Cordeiro won Miss Singapore Universe in 1999 but is humble about her achievement.
"It could have been the result of the other girls not preparing well for the question-and-answer segment," the 38-year-old says.
When she joined the pageant at the age of 23, she was studying for two master's degrees.
The full-time research fellow at the University of Gothenburg, Sweden, says: "It was the inherent researcher in me that made me take part in the local beauty pageant.
"I was already progressing on the academic front and the beauty pageant gave me the opportunity to explore a different side of me - my self-presentation, public speaking and finding my personal voice."
Ms Cordeiro represented the nation in the Miss Universe finals in Trinidad & Tobago.
She has some words for those who say that beauty is the be-all and end-all in pageants.
"All sorts of questions were thrown at me in Trinidad," she says.
"Questions like: 'How can Trinidad follow Singapore's syllabus?' Not everyone can handle such questions with ease."