The Undertaker made a name for himself in the first decade of his WWE career in the '90s. During that decade, professional wrestling went through many changes. To ensure that he stayed relevant, Undertaker reinvented himself and evolved his character in the New Generation Era and Attitude Era.

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However, not every year of Undertaker's WWE career in the '90s was great. He had some terrible feuds and had his own injuries to contend with. Nonetheless, Undertaker won three WWF Championships in the 1990s, the most he has won in any decade of his illustrious career.

10 1990

Undertaker 1990

At Survivor Series 1990, The Million Dollar Man Ted DiBiase introduced Undertaker as his mystery partner to complete his team. The Phenom's slow eerie walk down to ringside with his Funeral Dirge theme in the background had everyone take note.

Brother Love accompanied Undertaker down to ringside, and it was evident that The Deadman was going to be a formidable force. It was the shortest year of his career in the '90s as he debuted in November but he had a solid performance, and it was a sign of big things to come.

9 1993

Undertaker 1993

Undertaker's 1993 was one of the worst years of his WWE career. The Deadman feuded with Giant Gonzalez for the majority of the year. Gonzalez was managed by Harvey Wippleman, but the issue with Gonzalez was that he lacked the in-ring skills due to his height and abilities.

The Phenom appeared on the first-ever episode of Monday Night Raw on January 11th, and he defeated Damien Demento in the first main event on Raw. Undertaker scored victories over Gonzalez at WrestleMania IX and SummerSlam. Moreover, at Survivor Series, Undertaker set up his feud with WWF Champion Yokozuna which would go into 1994.

8 1994

Undertaker 1994

1994 was the first year where Undertaker reinvented himself. At the Royal Rumble, The Phenom lost his WWF Championship casket match to Yokozuna. Undertaker had some injuries which he needed to heal and it was his first major hiatus from WWE.

Undertaker missed WrestleMania X, which was the first of three occasions that Undertaker would miss WrestleMania. Seven months later, Undertaker made his triumphant return at SummerSlam and he ditched his grey for purple. He faced off against the Fake Undertaker in the main event which he won. The Deadman closed out the year in another casket match with Yokozuna at the Survivor Series, but he was the winner this time around.

7 1992

Undertaker 1992

The Undertaker began 1992 as a heel, but once his alliance with Jake "The Snake" Roberts ended, he turned face for the first time in his WWE career. Undertaker remained as a face for six years, which revealed another layer in The Deadman's character.

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However, Undertaker's popularity grew and fans loved him. At WrestleMania VIII, Undertaker defeated Roberts after planting him with a devastating Tombstone outside of the ring. Unfortunately, Undertaker's 1992 would go downhill as he began a year-long feud with wrestlers managed by Harvey Wippleman. The Phenom had lackluster matches with Kamala at SummerSlam and Survivor Series with the feud culminating in the first-ever casket match at Survivor Series.

6 1995

undertaker-1995

In the mid-90s, Undertaker still had unfortunately poor feuds with wrestlers he tried to get over as opponents. For the majority of 1995, Undertaker had a rivalry with Ted DiBiase's Million Dollar Corporation. The Deadman overcame IRS at the Royal Rumble, King Kong Bundy at WrestleMania XI, and Kama Mustafa in a casket match at SummerSlam.

However, Undertaker suffered a crushed orbital bone caused by King Mabel's clumsiness in the ring. The Phenom began wearing a white Phantom of the Opera-like mask. He returned at the Survivor Series with a new rendition of his Graveyard Symphony theme. Undertaker got his revenge on King Mabel in a Casket match at In Your House 5: Season Beatings to round off another mediocre year in his WWE career.

5 1996

1996

1996 saw Undertaker's caliber of opponents improve drastically. At the Royal Rumble, Bret Hart removed Undertaker's mask in their WWF Championship encounter. Undertaker picked up a huge win over the soon-to-be departing Diesel at WrestleMania XII in an underrated clash.

However, the night after WrestleMania XII, Undertaker began a feud with Mankind. The deranged figure posed a formidable threat to Undertaker. At King of the Ring, Mankind upset Undertaker and he won their match in the Boiler Room Brawl at SummerSlam. Moreover, Undertaker's five-year partnership with Paul Bearer came to an end at SummerSlam as Bearer nailed Undertaker in the head with an urn and sided with Mankind. 1996 also saw the debut of the Buried Alive match in which Undertaker defeated Mankind. The Deadman also defeated Foley at the Survivor Series, Undertaker wore an awful black outfit but was victorious once more.

4 1991

Undertaker 1991

Undertaker's full debut year in 1991 was absolutely brilliant. The Deadman ditched Brother Love, who could not be committed to Undertaker as a full-time manager due to his commitments behind the scenes. Nevertheless, Paul Bearer began his successful alliance with The Undertaker. The Phenom won his debut WrestleMania match to kickstart his unbeaten WrestleMania streak at WrestleMania VII by defeating "Superfly" Jimmy Snuka.

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Undertaker feuded with The Ultimate Warrior, which showed that The Deadman could hang with the big boys. At Survivor Series, Undertaker capped off a sensational full debut year by defeating Hulk Hogan to capture his first WWF Championship. Unfortunately, Undertaker dropped the title back to Hogan six days later at This Tuesday in Texas.

3 1999

Undertaker 1999

By 1999, The Undertaker was back as a heel and he was the leader of The Ministry of Darkness. However, Undertaker's year was a mixed bag as he captured his third WWF Championship from Stone Cold Steve Austin at Over The Edge.

Undertaker's in-ring performances were not the greatest as he sustained a groin injury. Nonetheless, The Phenom won the first Hell in a Cell match at WrestleMania against The Corporation's Big Boss Man at WrestleMania XV, which was one of Undertaker's worst WrestleMania matches. Moreover, Undertaker took Big Show under his wing, and the two giants won the WWF Tag Team Championship twice before Undertaker departed in September to nurse his injuries.

2 1997

Undertaker 1997

1997 was another stellar year for The Undertaker. The Phenom captured the WWF Championship for the second time in his career in the main event of WrestleMania 13 by dethroning Sycho Sid. It was Undertaker's first reign with the gold in almost six years. Moreover, it was great that Undertaker held the WWF Championship for five months, considering Shawn Michaels and Bret Hart were his main contemporaries.

Undertaker reignited his feud with Mankind in a title match and retained the gold over the likes of Steve Austin, Vader, and Faarooq. However, Michaels accidentally nailed him with a steel chair at SummerSlam which led to Bret regaining the title. The Undertaker's 1997 culminated with a new foe to contend with in his half-brother Kane. The Big Red Machine cost Undertaker his number one contender's Hell in a Cell match at Badd Blood: In Your House with Shawn Michaels.

1 1998

Undertaker 1998

Without a doubt, 1998 was not just Undertaker's best year in the '90s but it was one of the best years in his WWE career period. The Undertaker came up short once again in a casket match for the WWF Championship with Shawn Michaels at the Royal Rumble.

Kane interfered and cost Undertaker the match. Nevertheless, Undertaker's in-ring matches were outstanding and got better and better. Undertaker defeated Kane in showdowns at WrestleMania XIV and in the first Inferno match, the following month.

However, his Hell in a Cell match with Mankind at King of the Ring was the standout moment of the year with the number of bumps that Mankind took. Undertaker briefly held the WWF Tag Team Championship with Austin in the summer, and they collided in a sensational WWF Championship match at SummerSlam with Austin retaining the title.

Moreover, by the end of 1998, Undertaker returned to his roots by turning heel for the first time in six years and reunited with Paul Bearer. The devious duo planted the seeds to begin The Ministry of Darkness which began at the start of 1999.

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