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I am new also and I struggled with this also but I finally got it figured out.
1. Close OOTP down
2. From the START button find the folder labeled Out of the Park Developments
3. From there follow this path: C:......\Out of the Park Developments\OOTP Baseball 14\saved_games\[Name of your game].lg\news\html\images\team_logos
4. In here you should see 8 logos of different sizes for each team in your league. Write them down exactly as they are written, you must used underscores instead of spaces. Don't worry about the number at the end. What we are after is the name. Example: boston_red_sox_
5. Delete everything in the team_logos folder.
6. If the logo you want is a .png of jpeg file just copy it into the team_logos folder and rename it EXACTLY as the team name you wrote down. With the appropriate suffix (.png or .jpeg) at the end.
7. If it is not a .png or .jpeg file then you need to convert it to one of those formats. I suggest .jpeg. (When I converted a .gif file to .png and then restarted the game, OOTP mangled the logo. Did not have that problem with a .jpeg file) To do this, right-click on the file and select Edit. Under the file menu select Save As... Rename the file and select .jpeg file type. Copy the file into the team_logos folder.
8. To change the league logo, follow the same steps except you would be in the C:......\Out of the Park Developments\OOTP Baseball 14\saved_games\[Name of your game].lg\news\html\images\league_logos folder.
9. Reopen OOTP and open your league. If all went well the logos should be there.
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