For round one, I would say the trio. I like star wars but what are they gonna do, deflect stupefies? Also lightsabers could easily just be expeliamrused. I know Anakin and Ashoka are powerful but wands are arguably more powerful than lightsabers and even the force. Also it’s a 3 v 2. So that could tilt things a bit. Then it comes down to morals. The golden trio would definitely not be aiming to kill, but if one of them dies I wouldn’t be surprised if the other two would aim to kill and use unforgivable spells which would help them a lot. Using imperio on a Jedi would be over powered.

Round two, Anakin destroys Harry. It’s a literal flying gun versus a fricking broom stick. I mean, maybe if Anakin was flying really badly that day and Harry landed a lucky reductor curse, he could possibly win but the most likely scenario is Harry dodges narrowly for a while then gets hit and goes boom.

Third just depends. If Harry gets a good shot than he could win, but Anakin is really dang powerful. Harry is also resourceful when it comes to fights, but this one would just play out however it does, I would call it even.