Ms Pauline Wee was born at KK Women's and Children's Hospital (KKH). She gave birth to her first child there 45 years ago.
She trained as a midwife at the hospital a year later and stayed on long enough to help deliver five of her grandchildren.
"I was at the bedside of my daughter and daughter-in-law when they were in labour and I helped to dry and wrap their babies," said the 68-year-old, who is now KKH's assistant director of nursing. "I can't describe the feeling."
A total of 2,241 people - all born at KKH - gathered at Bishan Stadium yesterday morning to break the Guinness world record for the largest reunion of people born at the same hospital.
Aged between seven and 84, they had to produce their NRIC as well as their birth certificate.
The feat almost doubled the previous record of 1,221, set by The Medical City, a hospital in the Philippines, in April last year.
KKH previously held another world record for 10 years - for being the largest maternity hospital, with a record 39,835 babies born in 1966.
Some of those "babies" turned up yesterday to celebrate the 50th anniversary of the record with a cake-cutting ceremony.
"We are very heartened and humbled by the strong show of support from those born in KKH," said Associate Professor Tan Heng Hao, deputy chairman at KKH's division of obstetrics and gynaecology.
"The encouraging response... is a true testament to their appreciation for the holistic medical care and compassion that we provide to our patients every day."
Deputy Prime Minister Teo Chee Hean and Senior Minister of State Josephine Teo attended the event, which included a community carnival, where families played games such as giant Jenga and target frisbee.
Ms Wee, who worked in the old KKH building when she first joined in 1972, said the hospital has progressed much in terms of technology and research.
"Now, the women have more options to ease the pain of delivery. In my time, it was backbreaking as we could only have injections," she said. Her grandson, Callum, seven, who was born there, said: "It was like a hotel when I was warded for bronchitis. It is a special place."