A prominent feature of ankle sprains is their variable clinical course. The difficulty of providing a reliable early prognosis may be responsible for the substantial rate of poor outcomes after an ankle sprain. The aim of the present study was to evaluate the prognostic value of objective clinical measures, pain, and functional scores for ankle sprain recovery. Fifty-two participants suffering from lateral ankle sprain were included. Sprain status was assessed four weeks following injury and included evaluations of ankle range of motion, strength, function, and pain. Seven months following injury, a second assessment classified the patients into recovered and non-recovered groups using ankle ability measures. Following a predictor pre-selection procedure, logistic regressions evaluated the association between the four-week predictors and the seven-month recovery status. Twenty-seven participants (52%) fully recovered and 25 did not (48%). The results of the logistic regressions showed that walking pain was negatively associated with the probability of recovering at seven months (odds ratio: 0.71, 95% CI: 0.53–0.95). Pain four weeks after ankle sprain had relevant predictive value for long-term recovery. Special attention should be paid to patients reporting persistent pain while walking four weeks following sprain to reduce the risk of chronicity.