1. Tricking (SM, BW) vs 16. Gondra (ORAS) - Tricking has seemed dominant in SM OU especially as of late, coming off of a 7-2 snake record as well as having gained the most SM points in this stour. His ability to use more or less anything in the teambuilder, knack for innovation, and solid grip on the metagames will be able to give him the advantage in both SM OU and BW OU. However, I believe that Gondra has more metagame knowledge in ORAS OU and I've seen him play it a good bit in side tours, so I think he'll be able to steal a game from tricking.
2. Finchinator (SM, ORAS, BW) vs 15. Zokuru - Zokuru has gotten the vast majority of his points this smogon tour by stalling or cheesing his way to wins, and I know that Finchinator will be able to dispatch his bullshit with ease. I don't expect this to be a close series at all because Finchinator's no-nonsense approach to prepping and playing will give him a clear advantage over Zokuru that will be very difficult to overcome.
3. SoulWind (SM) vs 14. Bad Ass (ORAS, BW) - Soulwind is considered one of the best players of all time, but Bad Ass is a very hot player right now, having the most Stour BW points as well as coming off of a tour win in the last tour of the season, so I believe he'll be able to make the first upset of the tour. Soulwind's obviously excellent in all 3 tiers, but I believe Bad Ass's solid grasp of the BW OU metagame coupled with ORAS's less matchup-based metagame will favor him as the player that's been hotter down the stretch.
5. Empo (ORAS) vs 12. craing ;_; (SM, BW) - This was probably the hardest series to predict, since both these players are unpredictable and very solid at playing for the most part. Empo is an incredible player in all 3 of these generations whereas ben gay's knack for counterstyling his opponents is a large reason why he's been immensely successful lately, so realistically either of these guys could take it. However, I believe that ben will be able to generate a matchup advantage at preview that will be too much for Empo to deal with in SM and BW whereas the less matchup-centric nature of ORAS OU will favor Empo.
6. Ojama (SM, BW) vs 11. Welli0u (ORAS) - Ojama's been a dominant force in SM OU this year and has been a top 5 BW OU player for as long as I can remember, so it's very difficult to predict him losing in either of those tiers here due to just how strong a player he is. However, Ojama isn't very comfortable with ORAS OU, as it's easily his weakest gen, so the well is favored there with his relative comfort in the tier as well as him still being a really solid player overall.
7. xray (ORAS, BW) vs 10. FMG (SM) - FMG is a great player with a strong grasp on all three of these generations, but xray has looked untouchable in ORAS OU and has a slight edge in piloting the standard types of teams these two will likely bring in BW OU, but FMG is a very strong SM OU player and builder and I think he has the edge their. Aside from ORAS OU, I think both games will be very close and entertaining, so I wouldn't be surprised to see this series go either way.
8. z0mOG vs 9. Kickasser (SM, ORAS, BW) - z0mog isn't a bad player by any means, but Kickasser has just looked like a much better player in all 3 of these tiers in my eyes, having a versatility in teamstyles ranging from borderline stall to bulky offense and being at the top of his game playing-wise. I expect Kickasser to turn some heads in this tour and I think he can beat anyone in this tour on the right day, but z0mog is still a formidable player in his own right, so he could easily snatch a game or two and steal the series.