Only two, and it's been years ago now. I still sometimes take other people out hunting (mostly my sons' friends and their fiancees & such), but I haven't personally taken a deer in probably 5-6 years. Frankly, while I do a lot of shooting nowadays - as recently as today - I don't hunt much anymore.
For those two, I used the winchester PowerPointPlus load that's been discontinued since. It was a 64-grain moly-coated spire SP with a cannelure, and it ran almost as fast as 55-grain M193 stuff.
Winchester actually marketed it as a deer load:
and it worked great, at least on our admittedly small- to medium-size deer down here. Both completely thru-&-thru'ed the animals, doing an impressive amount of damage on the way.
Massive shame it isn't made anymore, it was a great load. When I found out it was being discontinued, I stocked up some and have probably 300-400 or so left now. It's still my primary go-to load for defensive purposes.