Urban flooding has become an increasingly serious challenge in many tropical cities due to rapid urbanization, increasing impervious surfaces, and the limited capacity of conventional drainage systems. Infiltration wells and injection wells have emerged as decentralized stormwater management measures to enhance infiltration and reduce surface runoff; however, comparative field evaluations of their hydraulic performance under tropical urban conditions remain limited. This study compares the hydraulic performance of infiltration wells and injection wells through field investigations conducted at four sites in Medan City, Indonesia, comprising two infiltration wells and two injection wells. Following natural rainfall events, water-level recession was monitored after rainfall had ceased and the water level had reached approximately ground level. Repeated short-term measurements (1-minute intervals over 30 minutes) and long-term measurements (1-hour intervals over 6 hours) were conducted to characterize the hydraulic response of the wells. Representative infiltration rates were determined by linear regression, while an exponential recession model was employed to characterize the long-term hydraulic behavior of the injection wells and estimate surrounding subsurface transmissivity. The results indicate that the investigated injection wells exhibited higher average specific infiltration rates, ranging from 1.37 to 1.58 cm/min, compared with 0.37 to 0.92 cm/min for the infiltration wells. In contrast, the investigated infiltration wells, which had larger diameters and cross-sectional areas, exhibited substantially greater observed volumetric recharge rates, reaching 4,599 cm³/min compared with approximately 250–290 cm³/min for the injection wells during the 30-minute experiments. The exponential recession model captures the observed long-term water-level recession behavior and provides a practical approach to evaluating injection-well performance. The findings suggest that both systems may have complementary roles in urban stormwater management. Injection wells may be advantageous where land availability is limited and rapid infiltration is required, whereas infiltration wells may be preferable where greater volumetric recharge capacity is needed, owing to the larger dimensions of the investigated wells. The findings further emphasize the importance of regular maintenance, particularly for injection wells, to control sediment accumulation, while stormwater pretreatment should be considered to minimize potential groundwater contamination. These results provide practical guidance for selecting infiltration technologies that complement conventional urban drainage systems in tropical cities.