Over the years I've won 6 or 8 guns in raffles, but the two big prizes I won were a Yukon Dall Sheep hunt, and an Alberta elk hunt. Both of those hunts were won at FNAWS raffles. The sheep hunt went well, shot a nice ram on the 8th day of a 10 day hunt. The elk hunt was a total, freaking, unabated disaster.
The ultimate raffle prize winner of all-time is a good friend of mine who is now 87 years old. The very first year that FNAWS ever held a raffle for a Mexican desert sheep hunt, he held the winning ticket and shot a nice ram. The following year, he won the same hunt again, after having bought only 1 ticket. Those made the 2nd and 3rd desert sheep of his hunting career, and if he were young enough to do it one more time, he'd have 4 grand slams if he took a 4th desert sheep.
When "I" won the Dall Sheep hunt, that gentleman sold my mother 1 raffle ticket, as my parents visited the sheep show for the day, mainly to visit with him. That one ticket my mother bought was the winning ticket, and since my mom doesn't hunt, I had to take the hunt for her. I felt it was the least I could do!