We fly long haul flights 5+ hours every month with our son. My advice: take the red eye. Play white noise while they sleep at home and put on some dim lights if possible to get them used to the noise and light of the plane. And shift their bedtimes earlier or later at home a couple days before to be closer to the time…

Your example, “When was the last time the United States missed the World Cup?” doesn’t seem to work on my Google Home.