The primary objective of this study was to compare assessments of health-related quality-of-life (HRQoL) in women who had a medical qualification for cesarean section (CS), depending on the number of CSs in their medical history. A short longitudinal study was conducted among 115 women on the day before a planned cesarean section (CS)-T1, and on the third day after CS-T2. They were divided into three groups. G1: no CS (n = 17); G2: one CS (n = 34); G3: two or more CSs (n  =  64). Participants completed a set of questionnaires concerning sociodemographic aspects and psychological outcomes: the HRQoL questionnaire (EQ-5D-3L). A chi-square test, McNemar’s test, and repeated measures ANOVA were used to compare the three groups in T1 and T2. Regardless of the number of CSs, before a CS, women mainly experience health problems with pain and anxiety/depression, and after a CS, mostly problems with pain, usual activity, and mobility. All participants experienced an increase in the amount of health problems with mobility and pain after a CS. Women who have had two or more CSs also had problems with self-care and usual activities. Women who have had one or two CSs experienced a decrease in the general assessment of the HRQoL, which is not observed in the group of women with multiple CSs. However, the HRQoL of women in the group with multiple CSs was lower before the CS than in the other groups. The results indicated the significance of the number of CSs, not only in postoperative, but also in preoperative HRQoL.