This is a class of question that I call "contradictory subjunctive". It takes a general form of assuming that this reality holds, with an explicit exception, and asks you to derive the consequences of the exceptional fact, in your actions or in the world. But it does not, as it appears to, probe for a necessary set of consequences. Instead, it subtly tests how much of one's reality one keeps intact in the face of a contradicting fact, and how much of it one bends to conform to the new fact, as well as which parts of reality one is willing to bend.
For example, one person might say, "If I had won, that would imply that I am, hypothetically, much better at math than I truly am. In that case, I surely would have won a scholarship from a tech school, and received a much better education than I have."
Another might say, "I know that I got questions six through eight wrong, so if I had won, that means that Jeremy Bem and the other forty people who did better than I did all died on the way to the competition. I would grieve for them, if I knew."
And another: "I lost because, like everyone on my team, I stayed up partying the night before and got three hours of sleep. If I had won, I must have slept instead, which would have resulted from my being a social outcast among math geeks. This implies that I would have been a rude and boorish person, and upon winning I would probably make some crass, deprecating remark."
What do you change, and what do you preserve? That is the underlying query in such ostensibly unrelated questions as "How would the world be different if the ocean were pink?" and "How would you react if I started levitating?"