This is current Naruto and Sasuke from the latest Manga chapter. They get no prep time and no rest.
Round 1 - Konoha 11
Round 2 - Deidara and Kakuzu
Round 3 - Itachi(Healthy) and Kisame
Round 4 - Pain and Konan
Round 5 - All the Jinchuuriki (including Killer Bee)
Round 6 - Gokage
Round 7 - Tobirama(Can't use Edo) and Hiruzen
Round 8 - Alive Madara(with PS and Rinnegan)
Round 9 - Alive Madara and Hashirama
Round 10 - Jubito
Where do they stop at? And who do they beat with what difficulty?
1. No-very low diff, only threats are Sakura who will be dead by the time her chakra for byakugou is charged and Huge Chouji
2. Low - mid diff. Mid-high if deidara has some C3 ready.
3. Mid-high.
4. Konan is a non-factor, pain gets taken at very low diff, naruto is enough while konan eats amaterasu. He just makes BSM clones and one shots the majority. Deva and Preta and Animal's cerberus are the only factors.
5. BM Naruto can take them at mid-diff so with BSM and Sasuke very, very low diff
6. Low-mid, only threat is Onoki
7. Can both win on their own. Very low diff.
8. Mid diff. Potentially high depnding on stamina.
9. They stop here. Otherside wins mid-high.