I currently own a relatively stock '70 Boss 302, and over the years owned 68 coupe powered by a '70 351C-4V, a '69 GT350 (351W-4V) and 71 Mach 1 powered by a 315W-4V. All were four speeds except the Shelby and 3.50:1 geared.
The 351C-4V was the best engine of the group as far as outright ability to put big power to the wheels is concerened. It pulled well from 2000 RPM to 6000 RPM. The Boss 302 is very similar except less torque under 3200RPM and revs out much quicker. The Boss 302 feels about the same HP as the 351C but has a shorter powerband. Very fun to drive but takes more concentrated effort than the 315C to hook up. Too much RPM and tires break loose, too little and no torque for off the line pull.
The 351W's were solid performers but lacked the revability and wide open responsivness at high RPM's. Nice wide powerbands, hit the pedal and lots of torque from 1500RPM to 4500RPM. Easy to drive but the small valves limit the rev factor and build the horspower at lower RPMS.
Given similar cars, my experience is that a good driver with a Cleveland 4V will beat a good driver with a Windsor 4V everytime.