First battles are one-on-one. Second fight is a team battle.
Tsuna Sawada vs Naruto Uzumaki (sage mode/no kyuubi)
Mukuro Rokudo vs Sasuke Uchiha (No Amaterasu)
Yamamoto Takeshi vs Kiba Inuzuka
Gokudera Hayato vs Shikamaru Nara
Hibari Kyoya vs Shino Aburame
Lambo (20 year old/no timelimit) vs Kakashi Hayate (No Kamui)
Ryohei Sasagawa vs Sakura Haruno
__________________ If you try something stupid, and it works it ain't stupid.
I haven't read KHR, but from what I've heard they rape easily, since most of them are casually hypersonic and would blitz the hell out of the Naruto characters.
1. Tsuna would get effed up by Sage Naruto. Definitely.
2. Mukuro against Sasuke would be interesting, since if Mukuro can scratch him even once with his trident than he can possess his body. Also he can control anyone else he might have sliced in Konoha. Although in terms of pure hand to hand fighting, Sasuke would win.
3. This is probably pretty intense. Although if Kiba is able to transform into his garouga giant demon dog thing It's probably over.
4. Shikamaru would probably outmaneuver Gokudera, although in terms of strength, Gokudera would easily rape shikamaru with his one shot cannon.
5.Hibari vs Shino would be fun. I think Hibari would win in hand to hand, although Shino has his bug powers. But if Hibari had control of his box weapon, I'd go with Hibari.
6.Lambo against Kakashi is harder to call just because we haven't seen much of the 20 year old Lambo. but I think in terms of fighting, Kakashi takes the win.
7. Ryohei rapes with Maximum Gatling.