Winry Rockbell, Fullmetal Alchemist
Like Sakura, Winry can be considered a part of a three-man team (consisting of herself, Edward Elric and Alphonse Elric) where she is constantly being left behind, watching the boys from behind as they continue to rush forward in life. Also like Sakura, Winry eventually gains a determination to become stronger so that she may support Ed and Al in her own way, be it emotionally or through her superior mechanical skills. Winry and Sakura definitely share a similar role in their respective groups.

Although they don't really look the same, Sakura and Winry are both respected for their intelligence, are generally friendly and kind-hearted, and don't have a lot of tolerance for Naruto or Ed's antics... And on that note, they both also end up noticing how both boys have grown and matured so rapidly and begin to recognize them with a newfound respect.

I think if Sakura and Winry were to meet, they'd probably find that they share a lot of common ground and would be able to understand each other very well. ^^

Sohryu Asuka Langley, Shin Seiki Evangelion
Asuka certainly bares a huge resemblance to Sakura early on in Naruto; she's bossy, bitchy, unafraid to voice her opinions and treats Ikari Shinji like dirt. Both girls are really intelligent and beautiful and like Sakura, Asuka is head-over heels in love with a pretty cool guy. In the Evangelion manga, Asuka tends to be two-faced, acting sweet natured around her superiors. Sakura also acts like this at the beginning, showing her true hot-tempered nature to her peers while acting like a good girl otherwise.

I can't say that Asuka and Sakura would get along very well if they met... it'd be hard to say unless it actually happened. ^^