Hello there,
It seems that during
this match, at turns 12, 13, I (Glazou in the replay) outsped my opponent even without the trickroom set up.
and at some occurences throughout the match, having a Trick Room or not does not seem to play in my outspeeding. I've detailed the occurences below, and plausible non-bug explanations when possible, and explanation to why I think it is not a bug.
We see at turn 14 that even after oppo sets up Trick Room the previous turn I still outspeed both before and after the TR setup. there is no speed tie here, as my Marowak-Alola set is minimum speed (=85), which is lower than Cresselia's minimum (157). But at turn 18, he still outsped with his Lunar Dance.
It is safe to admit that my opponent was not holding an iron ball, in which case I believe he would not have been as surprised as I, and I believe he'd have told me.
Even supposing he was holding a light ball and a 170 speed set to reach exactly 85 speed and therefore be on a speed tie with me (which is a bit Farfetch'd but let's assume every non-bug scenario) it still occurs during the match.
Turn 24, his M ampharos outspeeds my magearna. Now this one we could assume he was not min speed, but from turn 27 is when there is no doubt possible. on first turn my Hoopa outspeeds Magearna, so far so good, for as long as he has under 148 speed it makes sense, but on that same turn he uses trick room, and I still outspeed him next turn.
and on turn 28, I outspeed his ampharos despite the trick room.
And while that could once more be explained by him having simply not minimum speed (and at turns 24-25-26 he outspeeds magearna which most likely means it is indeed the case), I think it once more seems pretty far fetched that all the other scenarios, on top of this one, do fit together.
While it is obvious that his mega ampharos had the bad investments and was not minimum speed, I don't think that on top of that, he had a exactly 148 speed on his magearna, on top of having exactly 170 speed + light ball on Cresselia, and while I could be wrong on that (after all,
as the page about PSD RNG says, a one in a million event does appear every week on PSD), I think the chances of just a bug are at least as low as this event occuring. But only looking up the opponent's sets would (dis)prove that. Personally,
I can guarantee you that I have min speed on all the mons on that team.
TL;DR : Trick room seems to not always register, as demonstrated by
this match.