This Trophy really comes down to Luck (or lack there of). However, given the large number of matches you will need to play to get the Outstanding Coach and other Trophies you will eventually have one of your players die in a match. Just be sure you don't use your Apothecary to prevent the players death.
You can expedite your players demise by selecting teams with low armor values like Elves (needed for the In Dodge we Trust Trophy), Skaven (needed for the Horned Rat Trophy) or Goblins from the Orc roster.