Fungicides are usually applied on strawberries to manage gray mold, induced by the fungal pathogen Botrytis cinerea. In this study, four reduced-risk fungicides (formulations of pyrimethanil, PYR, 175 mL/hL; boscalid, BOS, 80 g/hL; combination fludioxonil, FLU, +cyprodinil, CYP, 110 g/hL) were applied before harvest for the management of post-harvest diseases of strawberries. The resulting fungicide residues on the strawberry fruit were also quantified. Strawberry fruits were harvested at 0, 4, 8, and 12 days following treatment (dft) and kept at 20 ± 1 °C for 4 days or cold-stored for 7 days at 0.5 ± 1 °C, followed by a 4-day shelf life at 20 ± 1 °C. All fungicides significantly reduced gray mold, according to the McKinney Index. At 0 dft and 4 days of shelf life, the FLU + CYP completely prevented post-harvest strawberry gray mold, while PYR and BOS reduced the disease by 88% and 42%, respectively, in comparison to the untreated control. For the duration of experiment, fungicide residues were always below the maximum residue levels, and FLU was the most degraded, thanks to the enzymatic pool of the strawberries. Monitoring fungicide residues in strawberries is essential to provide the consumer information on the safety of this widely consumed fruit. The present study points out the safety of strawberry fruits for consumers, even if the treatment strategy implies the use of fungicide mixtures before the consumption, with fungicide levels always being below the MRL.