Mammography interpretation is challenging with high error rates. This study aims to reduce the errors in mammography reading by mapping diagnostic errors against global mammographic characteristics using a radiomics-based machine learning approach. A total of 36 radiologists from cohort A (n= 20) and cohort B (n= 16) read 60 high-density mammographic cases. Radiomic features were extracted from three regions of interest (ROIs), and random forest models were trained to predict diagnostic errors for each cohort. Performance was evaluated using sensitivity, specificity, accuracy, and AUC. The impact of ROI placement and normalization on prediction was investigated. Our approach successfully predicted both the false positive and false negative errors of both cohorts but did not consistently predict location errors. The errors produced by radiologists from cohort B were less predictable compared to those in cohort A. The performance of the models did not show significant improvement after feature normalization, despite the mammograms being produced by different vendors. Our novel radiomics-based machine learning pipeline focusing on global radiomic features could predict false positive and false negative errors. The proposed method can be used to develop group-tailored mammographic educational strategies to help improve future mammography reader performance.