Two questions:

1. How is a double match loss entered in WER?
2. What does a double match loss mean in Single Elimination? Are both players eliminated? Who gets the airfare/byes/prizes? And how do we decide who gets the first and who gets the second prize?

Also, if you could support your answer with rules, that would be great because I couldn't find anything in the Tournament Rules that would even explain how single elimination works.

I believe WER can't handle double match losses in single elim. just watch loss one this round and the other in the next round (effectively giving the player's next round opponent a bye).

It is appropriate to give both players the prize for losing in the round that they got match losses. It is only a problem for Byes and such if it happens in the final but that should be a very rare event as only a single infraction causes Match Losses and all upgrade paths end at GL.

As for the double ML in finals - both players should get prizes, because they weren't DQd, they just lost the match. I personally would use standings to determine who gets the first place prize and who finishes second and gets the rest.

Standings regularly don't exist in single elimination because if you start with 2^n players your first tie breaker is always the same as everyone else in the tournament and deciding things like that on second or third tie breaker is bad times. And frequently no one tracks match results in single elim so they don't even exist.

So you are likely to have standing determined by tournament entry order.

Petr asked about byes and airfare among others, and while I didn't write it, I thought about a GPT/PTQ single elimination portion, where you do have standings available and can use that information if necessary. However, it's very unusual situation and very corner-case scenario, so I would rather try to fit the solution to actual situation than try to find a catch-all solution.

True Sebastian, the vast majority of single elim rounds I'm involved in are LCT at a GP/Nationals so I always think of them first :)