I had to have a friend who also played the game for any other scores to show up on my tracking. To get this achievement, you need to manually track a feat by going into the menu, pushing RT to select the feats menu, and picking to track one that a friend has beaten you on. I tested it with a feat that I had already beaten my friend on, and it wouldn't unlock when I passed their record again. It had to be something they were already beating me on. Quite possibly it also has to be your own new record. The achievement unlocked the very moment that I passed my friend's record. Same for the friend. We used the one for driving a boat on land since that's not something you'd normally have a high record for. (Although funny thing with that: some boats don't work for it! We had to use the boats with a big fan on the back.)
Try to do this as early as possible so that your records aren't nearly impossible to beat.