Evidence from both hypertensive and normotensive individuals indicate that elevated blood pressure is associated with decreased pain sensitivity. The current study sought to experimentally raise blood pressure using 250 mg caffeine, and investigate its effects on the cold pressor pain experiences of 25 men and 25 women. In a placebo-controlled repeated-measures experiment, caffeine increased systolic and diastolic blood pressure, as well as producing more clearheaded and energetic feelings. Caffeine produced higher pain threshold and pain tolerance levels compared to placebo, and women had a lower tolerance to pain than men. Finally, a significant association was found between caffeine-related increase in systolic blood pressure and caffeine-related increase in pain tolerance. Furthermore, this association was the strongest in women. These results are discussed in light of future directions for pain and hypertension research.