© 2019, © 2019 Taylor & Francis Group, LLC. Background: The purpose of this study was to describe dentists’ training experiences relevant to pain management, addiction, and prescription opioid drug diversion and examine associations between these training experiences and dentists’ opioid prescribing practices. Methods: A Web-based, cross-sectional survey was conducted among practicing dentist members of the National Dental Practice-Based Research Network (PBRN; N = 822). The survey assessed pain management prescribing practices and training experiences related to pain management and assessment for addiction and drug diversion. Survey data were linked with National Dental PBRN Enrollment Questionnaire data regarding practitioner demographics and practice characteristics. Results: The majority of dentists (67%) reported prior training in pain management; however, a minority of dentists reported prior training regarding identification and assessment of drug abuse or addiction (48%) or identification of prescription drug diversion (25%). The majority of training experiences across all topics occurred through continuing dental education participation. Dental school training relevant to pain management, addiction, and identification of drug diversion was more prevalent among more recent dental school graduates. Training experiences were associated with prescribing practices. Conclusions: Results suggest that across multiple levels of training, many dentists are not receiving training specific to addiction assessment and identification of drug diversion. Such training is associated with greater consistency of risk mitigation implementation in practice.