You seem to be getting confused between heading and ground track.
One of us is. Here's a specific hypothetical case. Say your desired ground track is due west, and the wind is from the north. To keep from drifting south, you need to make your heading a little north of due west, say 275 degrees. So you apply right rudder and the plane yaws to the right. In a second or less, its heading is 275. At this point, you can do one of two things. (1) Neutralize the rudder. If you do that, your heading stays at 275 degress, and if that's the right heading to keep you from drifting, your ground track is 270. (2) Keep applying the rudder input you used to make the plane yaw to where its heading is 275. If you do that, the plane will continue to yaw, the heading will continue to change, the ground track will curve toward the north, and you won't get that trophy.
If this doesn't convince you, I give up. I've explained it to you as well as I can. I can't understand it for you.