The manga has Fate's ending, but the story doesn't stick to the Fate route. From what I heard, it has elements from UBW route during the progression of the story.

Thanks, good answer. I watched the 2006 anime again recently and was struck by how bad the fight scenes looked--almost DBZ levels of badness. My memory had somehow made them much cooler. There were some weird plot holes and threads that never went anywhere, too.

Sorry, but I can't vote this answer up. You state that Studio Deen adaptation is medicore (which I agree with) but advise to watch Ufotable's, which we know nothing about until it comes out. Ufotable has a history of both successful adaptations (Fate/Zero) and not so (Gyo comes to mind here).

We now know that Ufotable's adaptation follows Unlimited Blade Works. This preview guide based on the first episode says it's so-so as an entry point for new viewers, but still equal to Fate/Zero in terms of general quality. Now that I've watched (half of) Fate/Zero, I can say that Fate/Zero does pretty well introducing Rin, even giving her an episode of her own, so for people coming in cold who don't want to read the VN, I'd probably say start with Fate/Zero.

So, im super confused, should i watch the 2014 anime first? or watch stay night, then zero, then this new anime?

@Chiquis Everyone seems to agree you should read the VN first if possible. I watched the 2006 anime, then Fate/Zero. If you can't play the visual novel, I would say do the 2006 anime or Fate/Zero first; I wouldn't advise starting with the 2014 anime. If you have no exposure at all to the franchise, the 2006 anime is tolerable, and it might be good to start there so it's not as disappointing after Fate/Zero, which has much better production values and a story that gets going faster. You could also start with Fate/Zero without missing too much.

Not sure if the comment section is right for asking...but your advice so far was very good, so i hope you'll indulge my asking. i've read the VN fate route and ubw route and while i had a lot fun and all (thanks btw. i wouldn't have read the VN without your answer here), i really don't feel like hearing approximately the same story a third time. Do you think it is bearable to watch F/Z before reading/watching heavens feel? Since they spoil each other anyway, the order shouldn't count? Also, i read your spoiler section (damn me) so i already have a feeling of what's going to be spoiled.

@Matthaeus Well, here's the thing - since you've already read the Fate route, you already know most of the big "spoilers" for Fate/Zero (how the fourth war ends, who the Saber and Archer of the fourth war were, etc.). There's almost nothing in Heavens Feel that spoils Fate/Zero that isn't also in Fate. So in your situation, I would strongly recommend doing HF before F/Z.

I totally understand where you're coming from when you say you don't want to read the same story a third time - so let me just tell you that Heavens Feel diverges hugely from the other two routes, very early on. I'd suggest playing Heavens Feel to about day 4 or 5. If you're still bored, then sure, go ahead and drop it and watch Fate/Zero.

@senshin ok thanks! I'll try to stay away from fate zero for now (which is gonna be hard...).

For what it's worth, it looks like Kirtsugu's affiliations are disclosed (albeit not gone into detail) in the second UBW cour.

@senshin, Is there even a "Heaven's Feel" anime?

@Pacerier No, but ufotable has announced that there will be one, at some unspecified time in the future.

This diagram may give you some insight about the relationship of the different artworks about the Fate/ series.

@Atcold that diagram has a lot of inaccuracies which most stem from one incorrect point. Fate/Stay Night TV 2006 should NOT be the focal point because of the points i mention in my answer

I think that the diagram has been created with a chronological order in mind (hence the stemming from the 2006 version). I think that a graphical representation may help understand the relationship between all the stories.

For those who haven't watched the DEEN F/sn anime (the TV series) yet, don't take @senshin's answer into account because you'll miss master pieces by Kawai Kenji :D