Purpose: The objectives of this preliminary, longitudinal, and explorative cohort study were to assess changes in and the onset of osteoarthrosis (OA)-related pain in the temporomandibular joint (TMJ) and to address factors that might impact the development or reduction of associated pain symptoms. Materials and Methods: In this sex-matched study, 60 women were recruited (30 asymptomatic with a magnetic resonance imaging [MRI] diagnosis of OA-related TMJ changes, 30 symptomatic with accompanying MRI evidence of OA of the TMJ). All subjects underwent a baseline clinical examination and MRI assessment and were subsequently referred to a dental practitioner, who was informed of the diagnosis and further treatment where required. Not all subjects underwent dental treatment interventions. Following a mean 4-year period, subjects were reexamined clinically. Spearman rank correlation and Mann-Whitney U tests were used to evaluate possible correlations in reported pain level changes with the number of posterior occlusal contacts and new dental restorations placed between baseline and recall appointments. Results: The dropout rate was 28% (6.7% for symptomatic, 50% for asymptomatic). OA-related TMJ pain in symptomatic subjects decreased with time (pain reduction: −3.6 ± 3.4 on a 0 to 10 numeric rating scale); asymptomatic patients rarely developed pain. Conclusion: These preliminary results suggest that factors other than dental occlusion might play a role in the reduction of pain.