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Do you have all of the equipment actually equipped?
any trick you used to get it working or did you just keep asking and reloading the save until it worked?
To get it to start I just had to reload several times sadly, I tried to not do it too quickly and wait a little longer (like just waiting 30 secs or something rather than the wait function) incase it was an issue with kicking it off while the npc wasn't in the middle of some kind of action.
Then issues with the actual duel, first time I just had to reload nothing seemed to work, then it happened again but this time waiting an hour worked, just be ready as it threw me straight into the duel. I'm not sure if it's something to do with him needing to heal, or maybe time of day and the npc's normal behaviour trying to take over. The second time I was a bit earlier in the morning as I sped through all the other stuff since I'd already done it once.
Bring lots of schnaps and save every time you manage to progress I think aha
Also if you do get past it all, and do the quest eventually later regular tournaments might open up in the city, avoid them for now until they do some bug fixing on it, because they're riddled with the same kind of bugs too. I got through one part of it and the rewards were just generic decent armour and some coin, so not missing much.