In Season Five, Jakob actually completed the Gimble challenge faster than Andrew.
Similarly, Dean from Season 6 outperformed Andrew in the Trailer Challenge.
Sean did the same thing in the offroad challenge in Season 2
Aaron's public drive from Season Seven, which was almost perfect (aside from rolling through a stop sign early in the drive). Seeing him grinning from ear to ear as he drives as a normal driver for the first time since nearly being killed by a woman who failed to observe a stop sign was truly a magnificent sight.
Chris Ferguson, the "winner" of season 1, returns in Ever to perform a nearly flawless performance in the assessment challenge. He ends up being the first graduate of that season.
One of the final challenges on the Ever season finale was to reverse down a narrow pathway lined with cars, do a reverse slalom, turn around, then Do It Again Forwards. Kevin somehow manages to pass it flawlessly. It's unfortunate that the same couldn't be said of anything else he did...