The wrestling one is just somewhat off kilter? It's not outright transphobic, more just kinda silly. It doesn't reference gender as an identity as much. More so gender as performance I'd say. It's a comparatively brief portion of the episode compared with the Olympics based one. The rest of the episode is pretty great tho and is all about a misogynistic asshole getting his comeuppance from a downtrodden woman who's always been told that fighting is for boy's. It's actually a great episode.

The Olympics one is self evidently transphobic. The premise is he's not actually a woman, he's doing it to beat fembots at the olympics. In the episode he undergoes hormone therapy and sex reassignment surgery... well the robot versions of those things. He is portrayed as having done this purely to win at sports. There has long been an established hate conspiracy narrative about trans women transitioning to beat women at sports. It was around back then, and this episode plays into the narrative quite a lot.

Futurama is my favorite animated show of all time. I love it with all my heart and for literally about a decade I skipped the gender bender Olympics episode every single time it came up. But I've come to appreciate some aspects of its very transphobic very misogynistic narratives. It's not something I'd sit and watch for fun, but as time as passed some small moments have stood out to me as being kinda interesting deconstructions of what gender is and the complexities of personal identity. Like when bender struggles with the idea of "detransitioning", even if it's for the wrong reasons and doesn't accurately portray any kind of transfeminine struggle in a genuine light. You can tell they sorta had half an idea what gender identity was and the ways in which trans people struggle with it. But the motives are never gender in and of itself, it's never about who bender is but always what he gets from gender performances.

Make no mistake though. It's among the worst. Not because it's the most hateful vile episode of any animated show ever, but because it's Futurama. I hold that show to a very high standard, as do a lot of people. They punched down on trans and gender diverse people there. They had no reason to do that. They played into a frankly insane amount of misogyny to make it all fit together too, in a way they hadn't done as much with other episodes. Look at Kif, look at all his episodes and the many ways his character deconstructs gender and sex in positive ways that show tolerant and informed viewpoints. It's not like they didn't know how to handle gender complex characters.

But with that one episode they just really gave a big fuck you to gender diversity, to gender diverse people, to trans women, and broadly to gender and sexual minorities as a whole. The whole thing is profoundly disappointing to me to this day. It's not enough to ruin the show for me, I love the show way too much for that. But it's embarrassingly bad and dishearteningly bigoted from a show that I expect so much more from.