TrueSkill team matchmaking goes a bit further than just looking at your personal "known" TrueSkill it also takes into account all other peoples TrueSkill. For example in team games (Red vs Blue) TrueSkill will add the most certain Level data and the most uncertain level data it has about you as an individiual and sum that level information with those known from your team mates. Then it will do the same for any opposing team and try to match the best possible fit. Meaning if 2 out of 4 players in your team have an highly uncertain skill level, it could very well be that the "match experience" for you as a more "known player to the TrueSkill system" is pretty bad, since there is a chance you get matched up with either noobs, or dominating pros. However, TrueSkill, according to it's math made the right match. Keep in mind if you keep playing with this team for a long time, the match experience should (theoretical) get better. (leading to more draws over time)
As you pointed out different playlist keep track of their own level.
As for this topic, I wouldn't mind having a bit of a fix, I can not compete on any US/EU server playing from China with a not so stable ping ranging from 350 - 500.
While giving me a lower ping certainly brings out a completely different outcome.
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