As for the match, Sendo will lose for sure after this foreshadowing of the baton. We all know Morikawa wants it to be Ippo at the end, I just question the pacing...
Ricardo's quite old and looking to retire. It's like Miyata having massive issues with weight control and needing to move up a weight class. These matches shouldn't ever happen and if they do I don't feel that they'd actually be at their best.
Besides Sendo isn't the type to "pass the baton" to anyone. He wants his rematch with Ippo himself. If he can somehow defeat Ricardo then he's really setting himself up for another round with Ippo.
Alternatively, Sendo goes the distance and it somehow becomes a draw. Ricardo retires, his legacy preserved but ultimately not that challenged by Sendo. Then if Ippo and Sendo happens again, he might spar with Ippo for his preparation and get interested in coming out of retirement for one final match. Honestly though, from what we've seen, he basically pays no attention to fighters he isn't going to fight so this is all beyond wishful thinking.
So I'd say he has a shot. If Sendo doesn't get that belt though, I guess we'll see him get a ring and propose in front of his grandma while his face is all swollen from the fight. That's the foreshadowing I'm getting from this chapter.