I have Osceola’s complete history from the mid-1940’s till now, and a few spots from 1915 till 1945. 

Yea this was in the 50’s so they must have moved up to the OBC in the 60’s. I’ll get the exact dates later. 

Final score is not even a true statement how this game really went dillard was up 28-0 then 41-7 with 2 minutes to go in the game both desperation touchdowns was with our backups in 

You may be correct, but if they were we never played them from my 8th grade year ('61-'62) thru my sophomore year while in the Ridge before initially joining the OBC during my junior year ('64-'65).  Since I was a foreigner in Kissimmee back then only knowing baseball, I started buying the annual yearbook that included Jr. High and Sr. High to familiarize myself with my new classmates.  Just verified the schedule in each of them. 

I know they were both in the ridge conference together, but I’m not sure how long. I have all that info at home. I’ll see what I can find.