I’m slowly building my Cat and was curious to get some feed back on this. I have both engines laying around and would like some input. The car will have P/S 4 gear and disc brakes. Mostly stock except for the rims and engine as I don’t like molesting a nice old car.
Uhhh…what’s a “P/S 4 gear”?
Year and model of Cougar would be helpful, as well.
I’m guessing its a power steering 4-speed and disc brakes. Probably cheaper to build a windsor up, but I like clevelands, only because thats whats in the car!
Having had both in previous 69s I would have to say go with the Windsor. No real reason - just personal preference.
Is there a significant weight difference between the two?
Don’t know about the W, but the C I took out of mine was a heavy pig.
Go with the windsor. More aftermark parts available and a little cheaper to build the same hp.
You may spend a little more on the Cleveland but once you have had one, you will not regret it.
My thoughts as well.
Sounds like the windsor is taking the lead here.
If we are talking a '69 Windsor, then the swap into a 67 or 68 gets a lot easier. The early 351 Windsor has the radiator hose outlets on the right side to match up with the 24" 302 radiator. Generally this is the easiest swap. I did this on my son’s '68. Power wise I have to agree that the Windsor is cheaper and easier, but the Cleveland is a fantastic motor. My experience is that the Windsor has great low end torque, and the Cleveland will rev forever with a little work on the valve train.
They are both good engines, but in stock condition they are also very different. The 351W makes a good all round engine, but If you want a lot of fun driving I would say go for the Cleveland. It has a weak side and that’s the bottom torque, but once you get the thing over 2500 rpm it wakes up and it will give you a kick. Personally I would prefer a well built Cleveland over a Windsor any time.
When I swapped my 289 for a 351W, I started with long block core from a 1989 F350. The timing set cover and water pump from my 289 worked just fine.
My engine is 1994 based clear down to the timing cover, reverse rotation water pump and serpentine belt system.
For me, it was easier just to get a FE radiator… it came as a three row vs. two… and it had the water outlet on the driver’s side which is where I needed it. 
Brand new it cost me exactly $10 more than having my original 2 row radiator rebuilt the way I needed it.
The only minor hurdle I had was coming up with molded hoses to fit the transplant.
I should have posted the car is a 67. It currently has the Windsor in it. While I haven’t assessed the condition yet I’m assuming it’s rebuilable.
The Cleveland will fit as well in the 67. Since the Windsor is in the car now, what make you think it needs rebuilding? Im sure the motor mounts are the same between the Cleveland and the Windsor. What transmission do you have?
And the Cleveland can be a great street engine with darn good bottom-end torque as well; it all depends upon intake/heads/cam selection. A little bit of stroking -say, make it a “6.5L” (just to be conservative)- will change it’s whole personality.
But if you’re not building a high-rpm “race engine”, and you don’t already have a good Clevo block, and you’re on a tight budget; the “Wheezer” (sorry, picked it up on the “Clevelands Forever” Foirum) is a good way to go. 
Thanks folks. Well I have both complete engines. Now that I think about it both are 73’s. The Cleveland is 4bbl 4 bolt main with, of course, the big combustion chambers. I’ve got all the 4-speed stuff for it now ( except the tail housing, but no problem there) and the 9 inch rear. The crank will probably have to be replaced so I’m looking at maybe a 408 stroker. I’ve run the Windsors through the years but I have never had a Cleveland in one of my cars yet. I have it’s lil brother in my 65 2+2 and it ran pretty dang good in that light of a car. When the Winsors started gasping for air that Boss motor was just getting going.
With the 73 cleveland you will have open chamber heads. Get the right cam for it and it will put a big, BIG! grin on your face. What makes you think you have to change the cam? it could be just cleaned up depending, I guess what it’s been through. Go to this site if you want to build the 351C. The people there are cleveland nuts and know how to make the most out of that motor. They will direct you in the right direction. http://www.network54.com/Forum/119419/
Yeah, if you have 73 4v engine, you don’t even need to spend a lot of money on it. You already have a good performance engine. Swap the cam/lifters, the rod hardware, and the valvetrain. That’s it. No fancy aluminum heads needed.