Functional foods and/or their bioactive compounds playing a role in improving skeletal health have received considerable attention. The objective of the present study was to determine the extent to which certain functional foods as (1) whole, e.g., dried plum (DP), figs, dates, raisin, and blueberry, (2) fractionated, e.g., DP puree, DP juice, and DP pulp/skin, or (3) isolated, e.g., DP polyphenols, fructooligosaccharides (FOS), and beta-hydroxy-beta-methylbutyrate, forms reverse bone loss in an ovariectomized (Ovx) rat model of osteoporosis. Additionally, some of these components were tested in reversal of bone loss in combination. For this purpose, 180 3-month-old female Sprague-Dawley rats were divided into 15 groups (n = 12) and either Ovx (14 groups) or sham-operated (Sham, one group). Rats were maintained on a semipurified standard diet for 45 days after surgery to establish bone loss. Thereafter, rats were placed on one of the following dietary treatments for 60 days: casein-based diet (Sham and Ovx). The remaining 13 Ovx groups were placed on various treatment diets. Results showed that diets supplemented with 5% FOS + 7.5% DP was most effective in reversing both right femur and fourth lumbar bone mineral density and fourth lumbar calcium loss while significantly decreasing trabecular separation. There were no significant effects of treatment on serum or urine measures of bone turnover. Although other treatments were good at altering some bone parameters, none had the success in altering several bone health indicators as the diets supplemented with 5% FOS + 7.5% DP. The findings of this study suggest the combination of 5% FOS + 7.5% DP is capable of reversing Ovx-induced bone loss.