Streak Question
 

When did the WWE actually start acknowledging that Undertaker had an undefeated streak at 'Mania and start promoting it?

And, in your opinion, did the WWE "book" the streak, or did one day someone look through the record books and realize that UT had been undefeated at Mania.

I want to say it first came to the forefront after he beat HHH.

The first time I think they said anything about it was when he defeated Ric Flair at Wrestlemania 18...... I distinctly remember a bloody Undertaker looking at the camera after the match and raising 10 fingers in front of his face and either JR or King mentioning that it was his 10th WM win.....

I don't think the WWE booked it, but after a while realized and just went with it.

I remember them saying something about it when he faced Sid for the title at WM 13...and maybe even WM 12 when he faced Nash.

Jim Ross refers to the streak when Undertaker beat Triple H for 9-0 (WM 17, 2001) but they didn't actively promote it before the match. Promos and hype for their feud was more about Triple H being tired of having nobody to beat while Undertaker says he never beaten him before.

The year after him vs Flair (WM 18, 2002), WWE did promote the streak since it was the handicap match and at the time the biggest threat to his streak (WM 19 vs Big Show and A-Train, 2003).

Yes, Ross used to put over the fact that the Undertaker had never lost at Wrestlemania.

The streak just kind of happened. Jobbing to Snuka wouldn't have exactly done wonders for Taker's career and no way Giant Gonzalez deserved a win over the guy so, like others have mentioned, they just went with it. At first it was just an interesting tidbit then it evolved into a booking tool.

Ah, you mean the "Test push" ('Test' as in Andrew Martin) where the team saddles a guy with a string of victories making them appear like they're interested in the guy until they're distracted by something shiny and end up forgetting about the whole deal.

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Take a look at this video and thou shall be enlightened.