Welcome to the Base ^_^
This is actually the versus section, which isn't suited for threads like these (it's more for like, throwing shuriken at people if you get me). I
think that this would be more appropriate in this section:
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(be warned though, opinions can be harsh at times)
As for the topic at hand.. it's hard to tell xD. Nobody else has been hinted to have a possibility with Gaara other than the random no-name fangirls, so there's much less competition for Matsuri. However, you asked who will achieve their goal
first. If Naruto does end up with Hinata, than he's likely to be first. If he ends up with somebody like Sakura, than NarutoxHinata won't even happen while GaaraxMatsuri is likely, so they'd be the first.