I’m having dramas as well.
I will set off for head to head and the other car will just tun off in another direction.
Also it seems that the other car is allowed to cut the corners when I do by too much I get the missed checkpoint warning.
I’m on the Xbox One and there are no checkpoints for head to head races. There is only an endpoint to get to and how you do it it does not matter. If you pause to look at the map, the AI pauses as well which is rather nice. (I don’t think the pause feature worked that way in FH1).
I’ve been getting this as well (Xbox One). I get shown as being in 2nd from very near the start of the race, and then it comes up as 2nd when I reach the destination, along with the patronising lecture from ANNA about being more careful who I choose to race. However, I do then seem to be getting the credits & XP for winning, and my win stat does increase. Very odd.