Racing the Leech
Very rare2.3%ObjectiveMissable
You won a race against the guard nicknamed Leech.
Missable - it hangs on a branching choice in the associated quest: you have to steer the conversation toward challenging the guard Leech to a horse race, then win it. Pick the wrong dialogue and the race never happens. Save before the quest, take the race option, and make sure you're on a fast horse for the win.