Yep, I've been trying a few different methods to unlock this dang trophy. So far, nothing has worked.
Play now? Tried and failed...TWICE. I even switched the "Favorite team" to each team before playing a game, still nothing.
Connected franchise? Failed.
Offline franchise? You guessed it: FAIL.
My last-ditch effort as of right now may be a solution to the problem, though I have not tested it yet. Here's what I'm going to do:
Step 1: Create an offline franchise and select a team.
Step 2: Pick a starting point (I'm going with regular season), go into league settings, and then set the mode to Competitive, whatever difficulty you want, 1-minute quarters, and 10-second Acc. Clock.
Step 3: Once you start the franchise, scroll over to the final tab (settings I believe) and you should find league settings, gameplay settings, etc.
Step 4: Select the "user teams" option: from here, you can take control of every other team by pressing the triangle or "Y" button (it will say "new character"). It'll suggest that you take the head coach position.
Step 5: After taking control of each team, it's grind time. I would write down each team's name to keep track, but to each their own.
Step 6: Upon winning the final game needed for completion, the trophy/achievement should, in theory, unlock. On the other hand, if the trophy/achievement doesn't unlock then well...EA REALLY screwed up on this one.