The primary aims of this study were to determine acute and longitudinal relationships between static flexibility measures and running economy (RE). Seventy-one healthy recreational runners (34 males/37 females, age: 36.4 [12.4] y, body mass index: 23.3 [3.1] kg/m2) completed an aerobic fitness assessment (VO2max) based on self-selected half-marathon race pace (RP) and flexibility testing (standing toe-touch test and weight-bearing lunge test) at baseline and 2 to 3 weeks prior to an endurance running or multisport race (70 [21] d apart). Participants resumed self-selected training and physical activity between laboratory visits. Hierarchical linear regressions were used to assess relationships between flexibility and RE across timepoints, and pre–post changes in flexibility and RE. Interactions between age and flexibility, and experience and flexibility were also investigated. No significant differences (P > .05) were found between flexibility measurements and RE at RP from visit 1 to visit 2, nor were there any significant associations between RE at RP and scores on the weight-bearing lunge test or standing toe-touch test. However, there was a significant interaction between age and the weight-bearing lunge test on RE at RP (ß = −0.0270, P = .018) such that older runners with less flexibility and younger runners with greater flexibility were less economical at RP at baseline. Our findings suggest that reduced flexibility may decrease the energetic cost of running for older runners to a greater extent than it does for younger runners. When prescribing run training intensity and mileage, coaches and clinicians working with masters runners should be cognizant of the potential performance benefits of decreased ankle joint flexibility as well as the overall greater risk of calf injury in this population. Future research should consider the underlying mechanism by which age enhances the beneficial effects of decreased flexibility on RE.