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We investigate the dynamics of two immiscible fluids in a cross-junction via three-dimensional numerical simulations using the volume of fluid approach to track the dispersed phase's evolution. Different regimes, namely the dripping, squeezing, and jetting dynamics, have been observed for different dimensionless parameters, and we unveil a transition in regimes due to the concomitant interplay of capillarity, viscosity, and wettability. Our results reveal that hydrophobic channel surfaces favor a transition from squeezing to dripping behavior at a lower value of the capillary number. Moreover, higher viscosity ratios advance the process of squeezing, necking, and breakage on hydrophobic surfaces. A wettability–capillarity regime map is also presented that will have significant implications regarding the choice of substrate wettability, fluid properties, and flow rate in droplet dispensing devices.