Let's see equipment of their time. Both relied heavily on tactics and crazy formations. Both had skilled officers. Sun Tzu would in my eyes be better at pregaming the fight. Most of his art of war btw was how to win before the fight begins. Julius Caesar was gifted against spread out large forces and his formations usually held as did Sun Tzus. read more
The question is meaningless on the face of it. You haven't defined any objectives which would motivate this conflict. The nature of the objectives which lead to conflict would define the shape of how it might play out, this is especially true in the case of positing Sun Tzu as one of the generals. read more
Richard would win. Simply because he was from a more advanced era. They were well into the use of steel and plate armor during his reign while bronze was the metal of note during Alexander's days. read more