Itachi.Sakura
Pictures & more info to be added....
Firstly, the pairing Itachi and Sakura is abbreviated as ItaSaku in the Naruto fandom. This is a pairing that we can safely say will only appear in fanworks, reason being their world apart, Itachi being a missing nin and the murderer that made Sasuke suffer all these years; Sakura on the other hand, is a devoted kunoichi and a trusted pupil of Tsunade. Her strong feelings towards her teammates also made it impossible for Sakura to ever fall in love with Itachi - the guy who has hurt all those close to her (Sasuke, Naruto and Kakashi).
However, this is exactly why this pairing is popular in the Naruto fandom. They are totally opposite and you and I know that opposite attracts (If you are not convinced, take 2 magnets and bring the north and south pole together). You can't deny that they do look cute together to a certain extent.
Due to their differences, it is a real challenge to write a fanfiction on their relationship and I salute those who managed to succeed. The most common plot used is that Sakura is captured by Itachi due to her close relations with the Kyuubi (Naruto). You can say it is a rather cliche plot but if the author managed to pull it off well, it will turn out to be an enjoyable fanfiction to read. There are also many interesting plots that creative authors out there came out with, including many AUs (Alternate Universe). Personally, I do have a number of fanfictions that I will reccomend - Deception ; One Week ; Identity and many more . I haven't read through all the ItaSaku fanfictions in FFnet yet so I won't be able to give all good ItaSaku fiction titles.
So how possible is this pairing anyway? Even though I am a fan myself, I have to say the chance of this happening is near 0. They did meet once but there wasn't any interaction at all. If Sakura is as hot-headed as Naruto, she probably would have attacked Itachi; for more reference, look for the chapter itself. Sakura's blood was really boiling at that time and she had this determined look to beat up Itachi for making Sasuke's life a living hell.
Sometimes, I do wonder why I am so crazy over this pairing.