This study investigates the effects of the structured wheels’ geometrical parameters on the geometries of structured surfaces machined by grinding operations. First, the geometrical parameters of the structured wheels were determined. The resultant geometrical parameters of structured surfaces were defined and related to the designed operating condition, including the structured wheel and grinding process by mathematical and simulation models. The results showed that each wheel’s geometrical parameter affects the structured surface geometry at different rates. Grinding experiments were then performed to explore experimentally how the geometrical parameters of the structured wheel affect the geometry of structured surfaces and verify the modeling and simulation results and explanations. The results showed a remarkable compatibility between the predicted and machined surfaces and reflected the accuracy of the presented method for machining the structured surfaces by grinding.