I'm still not certain that I understand what you are proposing. So, you mean that the question in the second round of a cup week is who will qualify in the first part of the week? If that's the case, then it could work. But that kind of question is impossible to research so it would be more based on luck than on ability to research.
I'm actually not proposing anything my response is directed towards the previous post saying it could work if implemented, but of course there will be something issues here and there towards approaching the best way to put such question into play without possible exploitation or loop holes at first. However, as the boss already said there wouldn't be any need to worry about that, at least for now.
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The tennis question is really going to be tough, Alcaraz with a definite tough game, Struff have been really impressive in the past few weeks winning his last 7 games in straight set and most of them are against top class players like Auger-Aliassime, Rune, Taylor Fritz and Ugo Humbert, His last defeat was from Sinner. So, I'm might just wait this out without Alcaraz because he's got a cast around his injured right hand and I don't know if he's fully healed or would be able to play through it all week long, however there aren't too many tough potential match up on his side of the bracket, so it's a really tricky tricky decision here, could probably have been easier If Casper Ruud was on his side of the bracket, given the impressive form Ruud is currently on.