Background: Previous studies have reported that a higher dietary inflammatory index (DII®) score is related to a higher risk of mortality and conditions that result in functional disability, such as cardiovascular disease, dementia, and fractures. Although these findings suggest that higher DII scores would affect disability-free survival, this has never been investigated directly. The present study investigated the association between the DII score and disability-free survival. Methods: We analyzed follow-up data covering a 12-year period for 793 older adults (≥70 years) participating in a Japanese community-based cohort study. DII scores were computed on the basis of dietary intake and assessed using the Brief Self-Administered Diet History Questionnaire. Data on incident functional disability were retrieved from the public Long-Term Care Insurance database. We applied the Cox model for estimating the adjusted hazard ratios (HRs) of the composite outcome (incident functional disability or death) according to DII score tertiles (T1⁻T3). Results: The proportion of men was 47.3%; mean (SD) age was 75.2 (4.5) years. The 12-year incidence of the composite outcome was 65.5%. A higher DII score was related to a higher risk for the composite outcome: HRs (95% confidence interval) were 1.05 (0.84, 1.32) for T2 and 1.26 (1.01, 1.57) for T3 (p-trend = 0.040) compared to the most anti-inflammatory T1 reference (HR = 1.00). Conclusions: These results suggest that a pro-inflammatory diet might be a modifiable factor affecting disability-free survival in the older population. Additional prospective studies are needed to confirm this relationship.