Myofascial stretching is often prescribed in the management of musculoskeletal pain. However, the neural mechanisms contributing to a decrease in pain are unknown. Stretching produces a sensation that may act as a conditioning stimulus in a conditioned pain modulation response. The purpose of this study was to compare immediate changes in pressure pain thresholds (PPTs) during a low-intensity stretch, moderate-intensity stretch, and cold water immersion task. A secondary purpose was to examine if personal pain sensitivity and psychological characteristics were associated with the responses to these interventions. Twenty-seven (27) healthy participants underwent a cross-over study design in which they completed a cold water immersion task, upper trapezius stretch to the onset of the stretch sensation, and a moderate-intensity stretch. A significant condition x time effect was observed (F (8,160) = 2.85, < 0.01, partial eta = 0.13), indicating reductions in pain sensitivity were significantly greater during a cold water immersion task compared to moderate-intensity stretching at minutes two and four. Widespread increases in heat pain threshold and lower pain-related anxiety were moderately correlated with the response to the cold water immersion task but not stretching. Moderate-intensity stretching may not elicit a conditioned pain modulation response possibly because the stretch was not intense enough to be perceived as painful.