One way to think about the TrueSkill ranking system is that it attempts to identify the correct ordering of n players in terms of 50 skill levels. If each ordering is equally likely, a computer would need log2(50) many bits of information to uniquely encode the skill level of a player. Now, assume that 2 players play a Head-to-Head game.
Disregarding draws, the game outcome can provide 1 bit of information (which of the two players was the winner). Since each of these games requires 2 players, the system needs 2*log2(50) many Head-to-Head games per player. Note that the particular Head-to-Head games have to be chosen such that they, in fact, do carry one bit of information.
Interestingly, every match-made game where the game outcome is not predictable ahead of time ensures that the game is informative! In general, with k teams of m players in each team, one game outcome provides log2(k!) bits but it needs k*m players per game so in the most general case, the system needs k*m*log2(n)/ ...
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