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The following dialogue is between two chess players at the end of a game. Does it mean "you have lost 4 games so far, what is your idea about going for the 5th game and developing the competition to 8 games"?
Dialogue:
A: Checkmate! Care to try for best five out of eight?
B: No, Thank you.
The source: http://www.clockwork-comics.com/2012/09/06/i-like-the-way-you-think-schlumberger/
To me, it just seems A is asking for a match of 8 games. If you exclude the possibility of draws, you'll need 5 wins to win such a match. This is similar to the best-of-X formats used in playoffs in many sports.
In any case, it's not terminology specific to chess. You might have more luck on English Language & Usage or English Language Learners.
Essentially, you would not ask for "best five out of eight" unless you have, excluding draws,
But these together are mathematically impossible, as that would require 9 games.
It doesn't get better if draws are allowed.
The reply should be "best 5 out of 9."
