Assuncao vs Font
I don't feel like I have the best read on this one, but my gut is telling me that this is a winnable fight for Font. Assuncao's 3-1 record since coming back from ankle surgery and being off for nearly two years is a bit deceiving. He should be 2-2 at best as he clearly lost to Moraes and could be 1-3, as the Sterling fight was extremely close.
How much Assuncao struggled with Sterling in essentially a pure kickboxing matchup, makes me think that he's going to have similar problems with Font. Sterling and Font both fight long and even though the way they maintain distance is different (Sterling's kicks vs Font's jab), the blueprint is there for Font to stay on the outside and make it difficult for Assuncao to land his counters. Font throws a ton a volume as well, while Assuncao sometimes seems content with long periods of little activity. It's worth noting that both of Font's losses in the UFC have come against possibly the two best pressure fighters in the division. I also feel that Assuncao's footwork hasn't looked as good since he came back from the ankle injury.
My concerns on Font's side are his fight IQ and Assuncao's leg kicks. Font was hurt before he shot on Munhoz, so that mistake is excusable but there are other examples. Font had both Andrade and Almeida hurt on the feet and instead of looking to unload and put them away, he took the fights to the ground. He got away with it, and got the finish anyway in both cases but it's still not confidence inspiring. Also, against Lineker he didn't use his jab nearly enough, despite his corner asking him to.
As far as the leg kicks go, Font is going to naturally be vulnerable to them with his boxing stance, but we haven't seen anyone really make him pay yet. I noted before the Kattar (who happens to be Font's teammate and has a similar boxing style) vs Moicano fight that they could be the difference. In that case, we had seen Kattar have his leg compromised by lesser leg kickers than Moicano, but we don't really have the same type of evidence with Font (at least not that I've seen). The two more recent fights where Assuncao had success with his leg kicks was against Caraway and Lopez. But, Lopez is a southpaw and it was the inside leg kick that really did the damage, which won't be available against Font.
So, while it's hard to be super confident, I think Font has enough advantages on paper (age, length, speed, power) to where this should be a pick em at worst. Font is also the more likely finisher IMO. I think the most likely scenario is that this comes down to a close decision though, which is enough for me to go 1u Font at +150.