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In the current study, we sought to evaluate the effects of phosphoryl-oligosaccharides of calcium (POs-Ca) and/or fluoride-containing toothpaste on enamel. Six groups of experimental toothpaste were prepared by adding various concentrations of POs-Ca and/or fluoride. A 5 × 10-mm window on the enamel of the bovine incisor was immersed in resin and divided into three areas for “sound”, “demineralized (DEM)”, and “after pH cycle (aft. pH cycle)”. All specimens were subjected to pH cycling, including soaking in a slurry with toothpaste diluted threefold for 5 min. Transverse microradiography was employed to evaluate the mineral recovery, and the pH values of each demineralization solution were measured. The high fluoride concentration group showed a significantly better mineral recovery rate than the others, with no statistical differences between before and after pH cycling among the POs-Ca with low fluoride, POs-Ca only, low fluoride only, and control groups. In the low-concentration fluoride groups, the group containing POs-Ca tended to have a higher remineralization effect than the non-POs-Ca group. After pH cycling, the demineralization solution showed no pH changes in any group. The addition of POs-Ca and fluoride to toothpaste may recover the mineral density in enamel subsurface lesions at low-fluoride concentrations, but the high-fluoride concentrations did not show a meaningful difference in the two groups with and without POs-Ca.