In Good Company Trophy in Thronebreaker: The Witcher Tales

You should have no issues obtaining this. You do not have to play five of the cards in one round, it can be spread out among all three rounds. Make sure you have at least five character cards in your deck.

If you want to get this out of the way, bring your cards to the minimum amount of cards needed with all the character cards available in your deck. Find a fight and then keep redrawing until you have them in your hand or until you hit your limit. Play all the ones you can and then finish the round. If you were not able to play all five, try again the next round and if you didn’t obtain any character cards, lose the round, and try again for the third. If the other character cards didn’t get drawn, restart the game and redo the fight again until you get it.