He has good chances to lose all matchs.
Jirobo was significantly more stronger than Choji in base and i think that Shino wouldn't stand much chance against Choji in his butterfly mode. It all depends in which manner would Shino lose, this will be his biggest chance against S5.
Kidomaru was able to push Neji to his limits and Neji at that time was one of strongest Genins in Naruto (i estimate that he was much more powerful than Shino) and even he win this fight because of plot. I don't see that Shino would stand much chance here.
Tayuya win quite easily.
I always see Sakon and Ukon as stronger out of Sound 4, so i think that he win this comfortable.
Kimimaro and VoTE Sasuke stomps him and any other Genin in Leaf at that time.