Who do you think will win? For me, I say Sakura.
Here’s how I see the fight:

Itachi: …Haruno Sakura…I heard about you…*Sharingan activated*
Sakura: *Glare* (Itachi Uchiha! He’s the one who caused Naruto and Sasuke so much pain!) *Slams fist together* (Get it together Sakura! I’ll capture him and once I do, Sasuke will surely come back!)
Itachi: Didn’t Chiyo teach you anything about fighting the Sharingan..? You are alone here. You’re suppose to run…
Sakura: Why would I want to run?! I’ll catch you if it means bringing Sasuke back!
Itachi: … You are still obsessed with my brother…why..? Be betrayed his friends and left behind his village. He has gone rogue.
Sakura: Because of you he has darkness filled in his heart! If I can catch you, I’ll see him again!

Sakura charges in, summoning a large amount of chakra to her fist as she neared him. Itachi’s eyes were darkened by his bangs as he raised both hands out in front of him and released a series of black crows flying out towards the enemy. Sakura ignored the pain and aims her fist straight for Itachi to see that she killed…a patch of Crows?! They flew out in all dirrections and the surroundings turned white and the sun went black.
Sakura: (Damn it! Just have to concentrate…Kai! Release!)

Once the jutsu was said, Sakura broke from the illusion and ran for Itachi.
Itachi: (She is much more trouble than I have expected…Amaterasu!)
Itachi’s black flame of Amaterasu hit Sakura..but she turned into a log! Itachi looks from his left then to his right. There’s no sign of her anywhere but when he looks above, he saw her coming down on his with her heel full of chakra. Sakura performed a powerful falling kick and it broke Itachi’s neck and he imedietly dies…

That is how I picture it!