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Objectives: The purpose of this study was to identify risk factors for initial complicated Clostridioides difficile infection (CDI). Methods: This retrospective cross-sectional study included adult patients with initial episodes of CDI who received ≥72 h of CDI-active antimicrobials. Patients were categorised into one of two groups: complicated CDI or uncomplicated CDI. A total of 513 patients were screened for inclusion, with complicated CDI patients exhibiting abnormal abdominal CT findings or experiencing death within 30 days post-CDI diagnosis. Results: A total of 203 patients met the inclusion criteria, comprising 143 (70.4%) with uncomplicated CDI and 60 (29.6%) with complicated CDI. Complicated CDI patients were more likely to have been exposed to fluoroquinolones (48.3% vs. 30.8%; P = 0.017) and to carbapenems for a longer duration prior to CDI diagnosis (7 days vs. 3 days; P = 0.019). They were more likely to receive oral vancomycin (65.0% vs. 46.9%; P = 0.018) and rectal vancomycin (5.0% vs. 0%; P = 0.025) compared with uncomplicated CDI patients. Logistic regression identified previous fluoroquinolone exposure increased the risk of complicated CDI, while previous abdominal surgery decreased the risk. Conclusion: Almost one-third of included patients experienced a complicated episode of CDI as their initial episode. Further research is warranted to elucidate the extent of influence of prior antibiotics on the development of complicated CDI.