With his sights set on the World Heavyweight Champion Edge and wanting revenge and to reclaim his title, the Undertaker was a motivated man in 2008. The Undertaker entered the Royal Rumble seeking to win the match for the second consecutive year. Unfortunately, the Undertaker entered at #1. The man who drew #2 was Shawn Michaels and once again we got a preview of what a match could look like between the two icons. The Undertaker would eventually be eliminated by Michaels himself.
The #1 Contendership for the World Heavyweight Title was still up for grabs as Wrestlemania XXIV drew near. The Undertaker would enter a match he had yet to participate in: the Elimination Chamber. The Undertaker would dominate the likes of Big Daddy V, Great Khali, MVP, Finlay and Batista to earn his title match at Wrestlemania.
The Undertaker and Edge wound up being the main event at Wrestlemania. Edge vowed to retain his title and end the Streak. The Undertaker would defeat Edge and win the World Heavyweight Championship for the second straight year at Wrestlemania improving his record to 15-0. The feud between Edge and the Undertaker would continue well into the summer. Edge who was allied with Smackdown GM Vickie Guerrero made the Undertaker’s title reign miserable. Vickie forced the Undertaker to vacate the title and in a TLC match for the vacated title Vickie imposed the stipulation that if the Undertaker lost he would have to leave the WWE. Eventually, Vickie brought the Undertaker back, not as a favour to the fans but to destroy Edge who had turned against her in a Hell in a Cell match.
Later in the year, the Undertaker hadn’t forgotten what Vickie Guerrero had put him through and vowed revenge for all she had to put him through. When it appeared as though the Undertaker would extract him revenge the Big Show attacked the Undertaker. Undertaker and the Big Show would square off in a series of pay-per-view matches for remainder of the year. Also during this time, the Undertaker would appear on Smackdown squaring off against younger talents but the list of new challengers was dwindling leaving the question to be asked, what else was there for the Undertaker to prove in the WWE?