25 Days of Christmas Hacking Challenge
This may be a little late, as it started 18 days ago, but all challenges are still up, so there's plenty of time to do them. A new one will get released everyday between now and Christmas. Most of these are really entry level, but for someone trying to learn pentesting, it's pretty fun. Plus you can win things like an amazon gift card and pentest+ vouchers. I think for every challenge you complete, you get your named thrown into a drawing.