[txranger]

For the game to assign them automatically they have to be named correctly and in the following location prior to starting a new game:

C:\Users\your user name\Documents\Out of the Park Developments\OOTP Baseball 14\logos

Once a game has been created, you can manually assign each team by going to the team home page click on the Options & Ballpark, then on the Options page click on Edit Team Colors Logos and there you will select Load under the Team logo to manually assign a logo...

Or assuming the files are named correctly you can copy them to your saved game folder:

C:\Users\your user name\Documents\Out of the Park Developments\OOTP Baseball 14\saved_games\name of your saved game