9-0, 19-0 and 20-0 Triple H (WrestleMania XVII, WrestleMania XXVII and WrestleMania XVIII)
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Triple H is the only man to face The Undertaker thrice at WrestleMania and the first of the three bouts came on the seventeenth anniversary of WrestleMania when The Undertaker pinned Triple H after delivering the last ride.
A decade later, both these men faced off again at the grandest stage of them all in a No holds barred match and once again, Taker came out victorious through submission. In the following year, both these men faced off again inside the Hell in a Cell, with Shawn Michaels as the special guest referee.
With all odds against him, the Deadman managed to beat Triple H for the third time at WrestleMania.
The 14-time world champion, Triple H was also the founder of WWE’s developmental program, NXT and following its success, he was elevated as the Executive Vice-president of Talent, Live Events and Creative.
At present, he is a part of WWE creative direction and storylines and is also appearing on TV as a part of the Authority. He is currently feuding against Seth Rollins going into the 2017 WrestleMania.
10-0 Ric Flair (WrestleMania XVIII)
The streak reached the double-digit mark when The Undertaker pinned Ric Flair after delivering a Tombstone at WrestleMania 18 in 2002.
Without a doubt, Flair is one of the greatest to have entered the ring. After losing to the Phenom, Flair was a part of the Evolution Stable and had feuds with Edge, Spirit Squad, Carlito etc.
He is a 16-time world champion (though he considers himself to be a 21-time world champion) and is the only man to be inducted twice into the WWE Hall of Fame (one for his individual career and one as a member of the Four Horsemen).
A day after he was inducted into the WWE Hall of Fame in 2008, Flair wrestled his final match in WWE and lost to Shawn Michaels before he gave an emotional retirement speech the next day on Raw.
After his retirement, Flair had stints with Ring of Honor and TNA before announcing his in-ring retirement.
In the majority of 2016, he was by the side of his daughter, Charlotte, as the duo displayed heel antics in a bid to help Charlotte retain her Divas championship/Women's championship before the Queen turned on her dad.
Currently, the Nature Boy is portraying himself in a 30 for 30 documentary for ESPN and also has a podcast.
