A lot have come from men. Just today, a famous one involving Kevin Spacey.
Not sure I’ve come across many with female superiors but I am sure that situation is quite a bit rarer in the first place than the reverse.
Quite a lot of sporting events allow anyone to enter, but have limits on who can win the championship. For example, an Albanian Championship could allow an Elbonian to take part, but the top prize goes to the highest placed Albanian.
If you have a Boys’ championship, then a boy should win the championship. Not a man, woman, or girl, even if they are allow to compete for any reason.