Pain is a significant welfare concern within the dairy industry. Recognizing and managing pain are important factors for safeguarding animal welfare. A questionnaire was sent via post to Irish dairy farmers and large animal veterinarians to assess attitudes to pain and the use of non-steroidal anti-inflammatory drugs (NSAIDs) in pasture-based dairy cows. The questionnaire could also be completed online. A total of 1,002 surveys were received from dairy farmers and 116 from livestock veterinarians. Veterinarians and farmers generally perceived the same conditions and procedures as the most painful. However, farmers scored surgical procedures significantly higher than veterinarians, and veterinarians scored lameness-related conditions, mastitis (clots in milk only) and hock hair loss significantly higher than farmers. Higher pain scores for conditions and procedures given by dairy farmers and veterinarians were associated with increased NSAID use. However, the use of NSAIDs was low, relative to the pain score, for Burdizzo castration (farmers and veterinarians), white line separation (farmers and veterinarians) and abscess (veterinarians), mastitis with clots in milk only (farmers) and calving with no assistance (farmers). Veterinarians who graduated less recently had significantly lower odds of using NSAIDs, and farmers that completed the survey online, had a larger herd size, completed education up to level four or five (as opposed to level three) and those who seemed to have less knowledge on analgesics, had significantly lower odds of using NSAIDs. Empathy was not found to be associated with NSAID use and no correlation was found between pain and empathy scores. Veterinarians perceived cost as more of a barrier than farmers did; therefore, NSAIDs should be offered more readily. For those working with dairy cows, there is a need to continue education on the benefits of analgesia, especially for conditions and procedures that have low NSAID use relative to pain score. The habituation of humans to pain in animals needs to be prevented to enable pain to be recognized and managed appropriately. Pain scores can be used as a benchmark for veterinarians and farmers to determine how their perception of pain compares to others, and see how this may influence their NSAID use.