I think that most insolvency practitioners take a sensible commercial view on things like this. I doubt anyone is going to have an issue over a trip, which could not be exchanged for cash in any case.
However, anything won that is tangible, and of material value, could possibly be grabbed by the IP.
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If you could pay the full amount - plus fee's & interest you would be debt free a lot earlier. If it took £10k to do this and your won £20k you would surely have ten grand left over for yourself. Suppose it depends on how much you owe on your original debt and how much you actually win.