This study has evaluated the runoff and erosion rates in torrents of Southern Italy, two forested headwaters with very similar climatic, hydrological and geomorphological characteristics; in one headwater, 15 check dams were installed in the mid-1950s, while the other is not regulated with engineering works. To this aim, the hydrological variables have been modeled over 15 years after check dam installation using the HEC-HMS (Hydrologic Engineering Center-Hydrologic Modeling System) model coupled to the MUSLE (Modified Universal Soil Loss Equation) equation. The model simulations have shown that check dams have not played a significant role in reducing the surface runoff compared to the unregulated torrent; in both catchments, the well-developed forest cover determined very low runoff coefficients (lower than 0.3%) with a scarce runoff generation capacity. Additionally, the reduction in peak flow due to the check dams was not significant, on average −7.4% compared to the unregulated headwater. Check dams have retained sediments for about 8–10 years after their installation, reducing erosion by about 35%, although soil loss was much lower than the tolerance limit in both catchments. After the sediment retention capacity of the dam sediment wedge was depleted, the sediment yield in the regulated torrent was even higher (by about 20%) compared to the unregulated catchment. Overall, the study has shown that the use of check dams as a catchment management strategy of forested headwaters under semi-arid Mediterranean conditions should be considered with caution, since the structures could be ineffective to reduce water and sediment flows during floods or, in some cases, check dams may increase erosion rates.