Background Acute diverticulitis is a common cause of hospital admissions and is associated with significant morbidity. Identifying factors associated with representation may help guide risk stratification and management strategies. Methods This retrospective case–control study examined presentations to St. John of God Midland Hospital with CT-proven acute colonic diverticulitis from 2022 - 2024. Cases were defined as patients who represented with diverticulitis to any WA public hospital > 30 days after a previous admission, while controls were patients who did not represent. Cases from 2025 were excluded to ensure a minimum follow-up period of 12 months. Variables extracted included demographics, smoking and alcohol status, Charlson Comorbidity Index, immunosuppression, number of previous episodes, peak CRP, Hinchey classification, disease location, length of stay, antibiotic use, type and duration, anti-inflammatory use, drain insertion, and surgical intervention. Statistical analysis was performed using SPSS and significance was defined as p < 0.05. Continuous variables were analysed using independent t-tests or Mann–Whitney U, and categorical variables using Pearson’s chi-square, Fisher’s exact, or Monte Carlo chi-square tests. Results A total of 157 patients were included (case group n = 86; control group n = 71). The number of previous episodes differed significantly, with cases more likely to have had multiple prior episodes (p < 0.001). The case group also demonstrated a higher Hinchey classification, although this did not reach statistical significance (p = 0.055). No significant differences were observed for other variables examined. Conclusion Patients who represent with acute colonic diverticulitis are more likely to have experienced multiple prior episodes, consistent with published data. While a trend towards more complicated disease was observed, the relationship between recurrence and disease severity remains inconsistently reported in the literature.