-Jirobo
He could not contend with the tiejitsu, but might be able to pull off a genjitsu to knock him out. (win)
-Tayuya
No way could he counter he flute unless he broke it. I assume he could keep dodging the puppets... but genjitsu would overpower him. The only thing that might work is setting a trap for her to fall into with metal line and kuni.... (overall loose)
-Sakon/Ukon
he would at least see their chakara enter his body and that they have multiple chakara sources... plus if Kiba figured out how to draw with them im sure sasuke could figure out a clever way to beat him. (win/draw)
-Kidomaru
Spiders would overwhelm him.... so he could negate that with his fire ninjitsu. He has no way to counter getting stuck in the web and as for the bow he might be able to dodge it by changing its trajectory and using his sharengun to anticipate it. (most likely loose)
Would win 1/2 the battles... not bad for his age.