Background: Preoperative, noninvasive prediction of meningioma grade is important for therapeutic planning and decision making. In this study, we propose a dual-level augmentation strategy incorporating image-level augmentation (IA) and feature-level augmentation (FA) to tackle class imbalance and improve the predictive performance of radiomics for meningioma grading on Magnetic Resonance Imaging (MRI). Methods: This study recruited 160 consecutive patients with pathologically proven meningioma (129 low-grade (WHO grade I) tumors; 31 high-grade (WHO grade II and III) tumors) with preoperative multisequence MRI imaging. A dual-level augmentation strategy combining IA and FA was applied and evaluated in 100 repetitions in 3-, 5-, and 10-fold cross-validation. Results: The best area under the receiver operating characteristics curve of our method in 100 repetitions was ≥0.78 in all cross-validations. The corresponding cross-validation sensitivities (cross-validation specificity) were 0.72 (0.69), 0.76 (0.71), and 0.63 (0.82) in 3-, 5-, and 10-fold cross-validation, respectively. The proposed method achieved significantly better performance and distribution of results, outperforming single-level augmentation (IA or FA) or no augmentation in each cross-validation. Conclusions: The dual-level augmentation strategy using IA and FA significantly improves the performance of the radiomics model for meningioma grading on MRI, allowing better radiomics-based preoperative stratification and individualized treatment.