This study examines how surfaces with different water contact angles (wettability) affect dry and underwater adhesion and friction. These studies were conducted by bringing a deformable hydrophobic poly(dimethylsiloxane) lens in contact with surfaces of gradient wettability. On the basis of our adhesion and friction results, we divide the results in three regions. In region I (water contact angles greater than 80°), the dry adhesion is lower than underwater adhesion. In contrast, in region III, (water contact angles less than 50°), the dry adhesion is higher than underwater adhesion. For surfaces with water contact angles between 50 and 80° (region II), the dry and wet adhesion values are comparable. Interestingly, in this region II, the underwater coefficient of friction (COF) values are higher than those in regions I and III. We have used surface-sensitive sum frequency generation (SFG) spectroscopy to probe whether the contact interface in static conditions and during dynamic sliding is dry or wet. The SFG results reveal that the contact is dry in region I. If this dry contact is maintained, the underwater COF follows the trend of adhesion hysteresis in dry conditions (adhesion hysteresis decreases with an increase in water contact angles). In region III, the contact is wet and the underwater COF follows the trend for adhesion hysteresis in wet conditions (adhesion hysteresis increases with an increase in water contact angles). By knowing whether the contact interfaces are dry or wet, we can relate the trends in COF with the trends in adhesion hysteresis. For conditions where the contact interfaces have both dry and wet patches (region II), the COF values are higher than those in completely dry conditions, suggesting that a partially lubricated system can exhibit a higher COF.