This study experimentally investigated Free-Fall Gravity Drainage (FFGD) under combination-drive conditions in a two-dimensional Hele-Shaw model representing a water-drive reservoir. An initially high gravity potential from the oil column enabled early oil drainage before aquifer support became dominant. Three water-drive strengths were tested, demonstrating that a stronger aquifer (1.15 psig) accelerated oil recovery to approximately 75% of the original oil in place (OOIP) within 60 minutes, resulting in a final recovery of 79.5%. However, this was accompanied by rapid water breakthrough after 2.5 minutes and high-water cuts exceeding 90%. In contrast, a weaker aquifer (0.725 psig) stabilized the oil–water contact, delaying water encroachment and maintaining zero water cut throughout 240 minutes, albeit with a lower ultimate recovery of 70.2%. Visual observations confirmed that a stable water crest and oil bank were preserved longer under moderate to weak aquifer pressures, extending the gravity-dominated recovery and reducing water handling requirements. Residual oil saturation was higher under weak aquifer support (27.9%) than stronger water drive (16.8%) due to a loss of gravity potential as the oil column declined and limited aquifer support. A comparative experiment in a heterogeneous system revealed approximately 22% lower ultimate recovery and water breakthrough within 5 minutes, attributed to heterogeneity promoting preferential flow, poor sweep efficiency, and early breakthrough. In contrast, the homogeneous system sustained production with no water breakthrough for 300 minutes. These insights strengthen the understanding of gravity drainage and can help guide enhanced oil recovery strategies in water-drive reservoirs.