Background/Objectives: Maternal nutritional status is a “key” contributor to Gestational Diabetes Mellitus (GDM). However, the role of maternal dietary patterns (DPs) during pregnancy remains poorly understood. Thus, we conducted a systematic review to assess associations between “a posteriori-derived” DPs and GDM. Methods: A systematic search was conducted in PubMed, ScienceDirect, Web of Science, and Scopus for cohort, cross-sectional, and case–control studies published until June 2024. A total of twenty-eight studies involving 39,735 pregnant women were included, and their quality was evaluated by the Newcastle–Ottawa Scale. The 91 identified DPs were classified into four categories: “Westernized”, “Nutritious”, “Plant-based”, and “Miscellaneous”. Results: Our findings do not reveal definitive associations between maternal DPs during pregnancy and GDM risk. Notably, “Westernized” DPs tended to be associated with an increased risk. However, a very small portion of patterns within this category exhibited protective associations. Conversely, “Nutritious” and “Plant-based” appear beneficial for GDM prevention in specific populations. The “Miscellaneous” category presented an almost equal distribution of DPs with both detrimental and protective associations, pinpointing the absence of a clear directional trend regarding GDM risk. Conclusions: The heterogeneity in findings can be attributed to geographic and sociocultural variations and methodological differences across studies. Thus, there is a need for more standardized research methodologies to provide more precise insights that will ultimately help develop effective and tailored dietary guidelines for GDM prevention.