"[3] Smillie was initially educated as a teacher and worked until age 25[4] to save for tuition for the Ontario Medical College for Women.

[6] Medical internships in Canada were difficult for women to obtain;[4] no hospital in Toronto would take Smillie as a resident intern, forcing her to move to the United States to complete an internship at the Women's Medical College of Pennsylvania in the city of Philadelphia.

Thus, she went back to Philadelphia for six months of intensive training under another female surgeon, which included a week where she oversaw a surgical ward, an experience which she credited with building her confidence.

[4] Prior to a building being built, the hospital was located inside rented houses,[3] and its early financial difficulties led the founders to gather vegetables from farmers' wives to feed their patients.

[7] She joined the Women's College Hospital in 1912, shortly after its creation, where she went on to become Associate Chief of Gynecology, a position she held until 1942.

[12] However, early civil rights activist Viola Desmond was chosen to be the first woman—and black person—to be honoured in this way.

[13] In 2023, Halifax artist Jo Napier completed a portrait of Smillie Robertson, which currently[14] hangs in the waiting room of the gynecologic oncology clinic of Halifax’s Queen Elizabeth II Health Sciences Centre.