Objectives This study analyzed the practices and findings on postpartum type 2 diabetes mellitus (T2DM) screening among pregnant women with gestational diabetes mellitus (GDM). Methods A retrospective cohort study was conducted at a tertiary care center in Western Saudi Arabia, between January 1, 2016, and December 31, 2018. It involved 642 nondiabetic women with a confirmed diagnosis of GDM, who were followed until delivery. Sociodemographic and baseline clinical data, as well as data on GDM and postpartum diabetes screening, were collected from the hospital's electronic records. The incidence of T2DM following GDM was calculated as the percentage of screened participants with a positive postpartum diagnosis, along with 95% CI. Factors associated with T2DM were analyzed using Chi-square or Fisher's exact tests, with significance set at p<0.05. Results The sample consisted of 642 women, primarily young and of Saudi nationality, with a notable high-risk profile including prevalent overweight and obesity (87.7%), multiparity (42.7% having four parities or more), and a frequent family history of diabetes (33.3%). Screening practices showed a great disparity between the proportion of women ordered for screening (466, 72.5%) and those effectively screened (130, 20.2%). Women who had cesarean sections were more likely to take the screening (25.0%) compared with those who had spontaneous vaginal delivery (SVD) (16.5%) (p=0.023). The incidence of post-GDM T2DM among screened participants was estimated at 13.9% (18 among 130). The incidence of post-GDM T2DM increased significantly among women with a history of three or more GDM pregnancies (50% vs. <12.5%; p=0.033) compared to their counterparts, respectively. Post-GDM T2DM was also associated with SVD (20.6% vs. 7.6%) compared to cesarean section, respectively (p=0.042). No further demographic or clinical factors were shown to be significantly associated with screening or postpartum diabetes. Conclusions There is a substantial gap in screening, combined with a high incidence of postpartum diabetes, among women with GDM attending our center. This highlights the urgent need for improved screening efforts, utilizing a risk-stratified approach to facilitate early detection and intervention, which could enhance long-term health outcomes.