Many diverse orientations of CH-p stacking interactions contribute significant stabilization to protein-carbohydrate interactions. This observation enables further evaluation of the role of CH-p stacking interactions in conferring selectivity for protein-carbohydrate binding and processivity in enzymatic reactions. In total, our studies reveal the molecular underpinnings of protein-carbohydrate binding interactions and the importance of improving molecular simulation forcefields and docking energy functions to account fully for this contribution.