If this is a game you are about to start upGo to the ootp 11 folder(c:my document/ootp 11/logos) and put the logos in there.
If the league is already started, go to (c:my document/ootp 11/save game.lg/news/html/images) and put the logos in there.
Here is the chapter in the manual for logos/uniforms
OOTP Baseball Manual - Team Colors, Logos, and Uniforms