Background: Our aim was to investigate the predictability of postoperative meningioma resection status based on clinical features. Methods: We examined 23 clinical features to assess their effectiveness in distinguishing gross total resections (GTR) from subtotal resections (STR). We analyzed whether GTR/STR cases are better predictable if the classification is based on the Simpson grading or the postoperative operative tumor volume (POTV). Results: Using a study cohort comprising a total of 157 patients, multivariate models for the preoperative prediction of GTR/STR outcome in relation to Simpson grading and POTV were developed and subsequently compared. Including only two clinical features, our models showed a notable discriminatory power in predicting postoperative resection status. Our final model, a straightforward decision tree applicable in daily clinical practice, achieved a mean AUC of 0.885, a mean accuracy of 0.866, a mean sensitivity of 0.889, and a mean specificity of 0.772 based on independent test data. Conclusions: Such models can be a valuable tool both for surgical planning and for early planning of postoperative treatment, e.g., for additional radiotherapy/radiosurgery, potentially required in case of subtotal resections.