Oldgens Predictions.
Cold Crew vs Church
SM: SMB vs kaori - Both were top players during the SM era, so we can be sure that both players have the level of competence to make this an interesting SM game. For this game, I have to give a significant edge to SMB; SMB has been active in the oldgens scene throughout the years, while there was a significant period of time where kaori was not only inactive in SM but also in competitive Pokemon in general. To put it bluntly, there is a possibility that kaori might be washed, but if they put in the reps and the adequate prep, this should be a good game.
XY: Akaru Kokuyo vs Yellow Paint - Akaru Kokuyo is the winner of the last DOU Classic and went 5-2 in the recent ORASPL, while Yellow Paint hasn't really made much of a splash in XY any time recently, not even participating in last year's XY Cup. They were both active while XY was CG, if I recall correctly, so they both should be mechanically competent. However, I'm giving Akaru simply because they havee actually played the tier, while Yellow Paint hasn't at all—and considering how XY is a format with some really particular teambuilding rules, being familiar with the metagame trends is a necessary edge. There also isn't even anyone in the Church that could provide meaningful support for modern XY, except maybe Nido-Rus. Unless Yellow Paint learns XY fast, or unless the Church can source a based modern XY team, I don't see this going well for them.
BW: Amaranth vs DaAwesomeDude1 - This is a bit of a similar story to the above, in the sense that Amaranth has actually played BW as of late (BW Cup Winner), while it doesn't seem as if Dad1 has played much of Pokemon at all. BW is a lot more forgiving, however, and judging from their own claims regarding their BW experience, Amaranth is also less of a daunting individual match-up. There is a difference in experience, which is why I'm giving the advantage to Amaranth here; however, that seems to be the only place where Amaranth's edge lies, as they haven't proved to be a teambuilder threat at all and thus this can really be anyone's game in the builder—perhaps SMB may help Amaranth with this? There is also the fact that this is still BW, which is definitely the most fickle out of all the oldgens. Should be interesting!
Cratermakers vs Sp_ndas
SM: Tman vs Nails - A highlight match for sure, as it's between two top-tier players. T "undrafted for DWC" man will be interesting to watch as this will be their first game within the community for what has been quite a long time. Nails, on the other hand, should be no stranger to anyone, particularly the zoomers, as they are a consistent, strong performer in OTTs. Judging this just by recent DOU experience, I'd have to give this to Nails. However, as Nails wrote in their sign-up post, perhaps their commitment to DPL may not be quite at a 100%; that's not necessarily a bad thing for the Sp_ndas, in the sense that an 80% Nails is still better than most of the DOU community, but I believe that Tman is in an interesting position as they should be just be around the same tier of skill as Nails while also likely trying a bit harder. This one should be close, and I'd love to watch this live but the likelihood of this game being tagged for @ Matches in DOUcord seems to be near zero.
XY: zee vs Mako - Mako used to be pretty fire in XY, solid and consistent, but that was a really long time ago. zee, meanwhile, is pretty fire now, but the that same fire does occasionally lead to them cooking too much. Should be a fun, even game to watch. I'm giving the edge to Mako here; while zee has the advantage in experience and understanding of what modern XY requires as well as in just not being washed, Mako does still have support from umbry and Z Strats, both renowned players that should be tangentially aware of the format's comings and goings. I do believe that this would be a bit of an upset, but the gap between the two shouldn't be that big, given Mako has adequate preparation.
BW: tennisace vs Lunar. - Both are crusty as fuck! However, if we are to compare the DOU resumes of these two players, it's a night and day difference as Lunar. actually has DOU achievements to speak of, even being a recent SCL draftee. tennisace, meanwhile, has never really had any standout DOU performances. Lunar. has the advantage of simply having higher peaks as a player and actually having recent activity in the DOU scene. Comparing the two's supports, zee alone is not enough of a difference maker, as even they still don't have that much BW experience and they alone would have to match the cache of umbry and Z Strats. Really, the one thing that can hold back Lunar. here is the voices in their head telling them to bring mono-Dragon; the Cratermakers have to hope they can adequately gaslight Lunar. into doing so before the game.
Spectral Thieves vs Storms
SM: Grandmas Cookin vs GenOne - This is a really weird game to try to make a prediction for. On one side, Cookin, Grandmas; 0-4 last DPL and went out R1 in SM Cup, with their one saving grace being a 3-0 SMPL run. On the other, One, Gen; possibly washed and hasn't played SM at a competitive level in what seems like a million years, their one team tour performance in the past year being a 1-2 attempt in DWC. Now, I ain't saying all these just to be a total dick; both are respected players within the community, with SM experience to their name, but as it stands there really isn't anything to write home about them. Narrative-wise, this is an interesting game as a win here will likely jumpstart the season of either player. I am only favoring Gma here purely for having more recent achievements, particularly as an SCL participant, but this is a game that both players will really want to win. Must watch!
XY: Croven vs raf - While not necessarily known for their ability to play modern XY, Croven is still a player with a significantly higher pedigree than raf, a player that is also not necessarily known for their ability to modern XY. Both have respectable supports for XY as well in Gma and Actuarily, respectively. There really isn't much to write about this: both are unknowns in this format, but Croven's peak as a player is well-regarded.
Taking the time here to recognize that it's interesting how Gma and Croven are flipped, as one would normally expect them to play the format of the other. Supposedly this is because Gma has a VGC event to attend, and since XY is a so-called builder's format, being slotted there when you don't have the time to prep would be unideal. However, as an XY player myself, I contend that a lack of prep time is not that of a big deal, and it's still fine to recycle and repurpose XY ideas. Taking Croven out of what seems to be their stronger tier is an interesting decision, and we will see how this will unravel soon.
BW: emma vs DaWoblefet - xD? DaWoblefet is supposedly the best BW player of the pool, behind Memoric, while emma is known more as a support than as an individual player. Don't get me wrong: emma can definitely play (I almost lost to them before!), but this is quite a difficult matchup, especially on the first week where data is relatively scarce. emma will have to prep out of their mind if they want to get this one, but it will still be quite the wall to surmount.