Due to its nutritional quality and palatability, chocolate milk beverages are gaining popularity globally. Alkalized cocoa powder is mostly used in its production since it provides for more intense color and dispersibility, but it has a negative effect on the phytochemical content of cocoa powder. Studies have suggested that water buffalo milk is superior to other milk due to its higher protein content and superior emulsion properties. As such, this study investigated the physico-chemical characteristics, sensory profile, and consumer acceptability of commercial and prototype water buffalo chocolate milk incorporated with alkalized and natural cocoa powder. Based on four buffalo chocolate milk samples, consumer acceptance was assessed by 120 consumers, which was combined with descriptive sensory data using a trained panel (n = 8) to determine drivers of liking. Compositional proximate analysis of alkalized and natural cocoa powders showed a significant difference in pH, moisture content, ash content, and fat content. Descriptive analysis showed that 8 out of 13 attributes (color, visual sandiness, cocoa and vanilla aroma, smoothness, creaminess, vanilla taste, and chocolate aftertaste) were effective discriminators of sensory attributes. Overall, buffalo chocolate milk samples were equally liked, but hedonic ratings of the individual attributes revealed that the samples were statistically different for color, viscosity (mouthfeel), and chocolate flavor. Partial least square regression (PLSR) identified chocolate flavor, viscous appearance, viscous mouthfeel, and bitter aftertaste as positive “drivers of liking”. The darker color provided by alkalized cocoa powder did not increase consumer liking. The purchase intention was equal for all chocolate milk samples, whether alkalized or natural. Both cocoa powders showed comparable performance in the manufacture of buffalo chocolate milk. Using natural cocoa powder may be beneficial to local producers of cocoa powder and cocoa farmers since it is easier to produce, while it can provide a marketing advantage for dairy beverages in the global trend of going back to “organic” and “natural”.