Background: The number of patients requiring reoperation has increased as the volume of hip arthroscopy for femoroacetabular impingement syndrome (FAIS) has increased. The factors most important in determining patients who are likely to require reoperation remain elusive. Purpose: To leverage machine learning to better characterize the complex relationship across various preoperative factors (patient characteristics, radiographic parameters, patient-reported outcome measures [PROMs]) for patients undergoing primary hip arthroscopy for FAIS to determine which features predict the need for future ipsilateral hip reoperation, namely, revision hip arthroscopy, total hip arthroplasty (THA), hip resurfacing arthroplasty (HRA), or periacetabular osteotomy (PAO). Study Design: Cohort study; Level of evidence, 3. Methods: A cohort of 3147 patients undergoing 3748 primary hip arthroscopy procedures were included from an institutional hip preservation registry. Preoperative computed tomography of the hip was obtained for each patient, from which the following parameters were calculated: the alpha angle; the coronal center-edge angle; the neck-shaft angle; the acetabular version angle at 1, 2, and 3 o’clock; and the femoral version angle. Preoperative PROMs included the modified Harris Hip Score (mHHS), the Hip Outcome Score (HOS)–Activities of Daily Living subscale (HOS-ADL) and the Sport Specific subscale, and the international Hip Outcome Tool (iHOT-33). Random forest models were created for revision hip arthroscopy, the THA, the HRA, and the PAO. Area under the curve (AUC) for the receiver operating characteristic curve and accuracy were calculated to evaluate each model. Results: A total of 171 patients (4.6%) underwent subsequent hip surgery after primary hip arthroscopy for FAIS. The AUC and accuracy, respectively, were 0.77 (fair) and 76% for revision hip arthroscopy (mean, 26.4-month follow-up); 0.80 (good) and 81% for THA (mean, 32.5-month follow-up); 0.62 (poor) and 69% for HRA (mean, 45.4-month follow-up); and 0.76 (fair) and 74% for PAO (mean, 30.4-month follow-up). The most important factors in predicting reoperation after primary hip arthroscopy were higher body mass index (BMI) and lower preoperative HOS-ADL for revision hip arthroscopy, greater age and lower preoperative iHOT-33 for THA, increased BMI for HRA, and larger neck-shaft angle and lower preoperative mHHS for PAO. Conclusion: Despite the low failure rate of hip arthroscopy for FAIS, our study demonstrated that machine learning has the capability to identify key preoperative risk factors that may predict subsequent ipsilateral hip surgery before the index hip arthroscopy. Knowledge of these demographic, radiographic, and patient-reported outcome data may aid in preoperative counseling and expectation management to better optimize hip preservation.