Background: Otogenic meningitis represents the most common and life-threatening complication of infective middle ear diseases. However, no guidelines are available to describe the optimal management strategy and the role of surgical intervention. Methods: A six-year multicenter retrospective study on consecutive patients treated for otogenic meningitis caused by acute otitis and re-exacerbation of chronic otitis at the University Hospital of Verona and Modena was performed, and a systematic review regarding acute otitis media-related meningitis in accordance with the PRISMA 2020 statement was then conducted. Results: From the clinical chart analysis, 16 patients with surgical indications according to our decision-making flow chart were reviewed, with most of them undergoing surgery within 7 days of admission (n = 13, 81%). The systematic review ultimately utilized 24 studies (16 case reports and 8 case series) published between 1990 and 2023, with the overall analysis involving a total of 181 patients. Conclusion: The primary treatment for acute bacterial meningitis relies on antibiotic therapy, with surgical intervention being employed in the event of complications and when the initial treatment is not effective within 48 h. The objective of surgery is to sterilize the tympanic and mastoid cavity, thereby eradicating the suspected infective foci and managing any eventual intracranial complications.