I have never come across ANY history questions in Battle of the Wits, so here is what I am doing.
You can boost this by yourself, and I have verified that it counts toward your total.
First pick "New Game", then "Homeroom". Set the CPU Skill Level to whatever you'd like.
Once the game loads skip past EVERYTHING until you can see the board with all the question available. If you do not see a history question you can answer, pause game and pick "restart". Keep doing this until you see a history question.
Once a history question actually comes up (World History or U.S. History), pick it and google the heck out of the answers if you do not know it. As soon as you confirm you got it right, and go to the next question... pause game, click restart, and rinse and repeat.
As long as you get the answer correct, you can keep restarting as many times as you want, and they ALL SAVE TO YOUR REPORT CARD. You can verify this yourself by checking back every so often as you wish.
Hope this speeds things up for you since if you had the same luck as me, this was one of my last achievements.