Both are pretty intelligent and try to go in for the kill fast. Which version of Obito are we using for this ? Rinnegan + Sharingan would be a better match, having the sheer versatility of Kamui and the firepower (CT, ST, Asura path) with some hax (that soul sucking path and the question path). Sharingan would have an harder time though. I'd still give it to Lille, since idk how another intangibility would react to Kamui. Really a match of speed, and I think that Lilel has Obito beat in that.
Rinnegan makes it easier though, since Obito could probably quickly snatch Lille's soul if he gets his hand on him.
Round 2 is harder, but Obito lacks Kamui and is stupid. He should be able to walk out of anything short of an headshot tho, thanks to the Regenerationn (by scaling from Madara though). Lille is also permanently intangible, so a blitz + TSB wouldn't work. If TSB doesn't work on intangibility, Lille takes it. If not, Obito could pop in and surprise Lille with a brutal and swift attack, but could lose if Lille use a significantly powerful move.
Round 3, well, Obito probably cannot hit Lille if he has perma intangibility. That said, I'm sure he could dodge the bullets. Those royal guard dudes reacted to them enough to try to block them, after all. He shoudl learn from his mistake if he survive a shot (which is likely, Kyoraku was able to move after taking them, the Regenerationn and much more durable Juubito should). I don't think he has ways to harm Lille, who can use Trumpete to attack (unless Trumpete lacks X-Axis property, at which point, Obito easily tank it).
I could see him going for a blitz with TSB at this point, if they can hit intangible beings.
