When Pitching Reigned Supreme: The 20 Legends of the 1990s

Last Updated: September 2nd, 2026 by Michael Schatz

The 1990s were a turbulent time in the MLB. Steroids were almost a requirement to become a star. Numbers ballooned in many facets. For pitchers, it normally led to higher ERA numbers. That's why the pitchers on this list are so impressive.

When baseballs were flying over the wall left and right, having the ability to stop that became that much more valuable. Here's our list of 20, and we're starting out with a good one.

20. Dennis Eckersley: The Closer Who Changed the Game

Dennis Eckersley was right in the middle of his legacy-building dominance when this decade started. He accumulated 293 out of his 390 career saves in the nine seasons that he played in this decade.

His signature Cy Young and MVP season came in 1992 when he led all of baseball with 51 saves on a 1.91 ERA while also winning seven games. Eckersley would go on to play out his career in St. Louis and Boston as he cemented his legacy as a Hall of Famer.

Dennis Eckersley — Career	Total
W	197
L	171
ERA	3.50
G	1071
IP	3285.2
SO	2401
WHIP	1.16
SV	390
MVP	1
Cy Young	1
All-Star selections	6
World Series titles	1

19. Bret Saberhagen: The Two-Time Cy Young Winner

We now recognize a great pitcher whose best days were behind him as he went through his ups and downs in the 1990s due to injuries. Bret Saberhagen still earned two of his three career All-Star selections in this decade as he went from Kansas City to Queens to Denver and finally to Boston.

It was quite a journey to end his career, as he still had his moments where he looked like one of the elite arms in the league.

18. Jimmy Key: The Quiet Craftsman

Jimmy Key was quietly in the upper echelon of starting pitchers throughout his 15-year career. He earned four out of his five career All-Star selections in the 1990s.

He saw some change in his career when he left Toronto after they won the 1992 World Series and joined the Yankees, where he ended up winning the 1996 World Series with them. That's pretty similar to another guy on this list and a former teammate of his, David Wells.

Jimmy Key — Career	Total
W	186
L	117
ERA	3.51
G	470
IP	2591.2
SO	1538
WHIP	1.23
SV	10
All-Star selections	4
World Series titles	2

17. Chuck Finley: The Angels’ Iron Man

Chuck Finley was just a workhorse through and through. He endured the highs and lows of being an Angel, spending 14 years of his 17-year career there.

That includes this entire decade. He was recognized for his efforts, earning three All-Star selections in the 1990s before moving on to Cleveland at the turn of the century. He unfortunately couldn't play in Anaheim for a couple of years longer, as they were able to win that magical World Series without him in 2002.

Chuck Finley — Career	Total
W	200
L	173
ERA	3.85
G	524
IP	3197.1
SO	2610
WHIP	1.38
SV	0
All-Star selections	5

16. Kevin Appier: Kansas City’s Underrated Ace

Kevin Appier may have been the most underrated pitcher of the decade. He only earned one All-Star selection and one top-three Cy Young finish. However, he won the ERA title in 1993 with a highly impressive 2.56 for the time. He also led all pitchers in WAR with a whopping 9.3 that season.

ERA+ weighs a pitcher's ERA against average pitchers of the era, where 100 is the baseline, and 130 is a Hall of Fame level. Appier built up a 131 ERA+ during the decade. Yet he seems to be forgotten.

Kevin Appier — Career	Total
W	169
L	137
ERA	3.74
G	414
IP	2595.1
SO	1994
WHIP	1.29
SV	0
All-Star selections	1
World Series titles	1

15. Andy Pettitte: October’s Left-Handed Legend

It's hard to believe that Andy Pettitte was only in his second year in the league when he led the Yankees to the 1996 World Series Championship.

He led the league with his 21 wins, and he started a postseason legacy that would only grow bigger as he got older. His best year of the decade was in 1997 when he went 18-7 with a 2.88 ERA in an MLB-leading 35 starts.

Andy Pettitte — Career	Total
W	256
L	153
ERA	3.85
G	531
IP	3316.0
SO	2448
WHIP	1.35
SV	0
All-Star selections	3
World Series titles	5

14. David Wells: Boomer’s Perfect Legacy

Let's stay in Toronto initially and highlight one of the more unique pitchers who found success in the 1990s. David Wells was a part of the 1992 World Series-winning Toronto Blue Jays. Then he went ahead and earned an All-Star selection in Detroit before getting traded to Cincinnati in the same season.

He then became an Oriole for a year before heading to the Bronx and enjoying more success as his 1998 All-Star season also turned into a World Series championship. All Boomer did to close out the decade was to return to the team he started it with in Toronto. Truly a journey where he got his money's worth.

David Wells — Career	Total
W	239
L	157
ERA	4.13
G	660
IP	3439.0
SO	2201
WHIP	1.27
SV	13
All-Star selections	3
World Series titles	2

13. Pat Hentgen: Canada’s Cy Young Hero

Pat Hentgen spent the entire 1990s with the Toronto Blue Jays, so he basically became an honorary Canadian. He rode the highs and lows with that franchise through the decade as they were able to have big World Series seasons mixed with some tough losing ones.

Hentgen carried them through as he had an amazing 1996 where he won 20 games and led baseball in complete games, shutouts, and innings pitched. Naturally, he won the Cy Young Award that year, which capped off his three All-Star selections in the era.

Pat Hentgen — Career	Total
W	131
L	112
ERA	4.32
G	344
IP	2075.1
SO	1290
WHIP	1.39
SV	1
Cy Young	1
All-Star selections	3
World Series titles	1

12. Jack McDowell: Black Jack’s Fierce Competitiveness

Short spurts can bring out some of the best pitching out of an under-the-radar pitcher. Jack McDowell had an amazing three-year burst from 1991 to 1993. He won 59 games combined in those three years. He also led baseball in complete games in back-to-back seasons.

In the other season when he didn't lead the league in complete games, he simply led it in shutouts. That was on his way to winning the Cy Young Award in 1993. He never really matched that success the rest of his career, but he absolutely deserves to be on this list for his stretch of dominance.

Jack McDowell — Career	Total
W	127
L	87
ERA	3.85
G	277
IP	1889.0
SO	1311
WHIP	1.30
SV	0
Cy Young	1
All-Star selections	3

11. Dennis Martinez: El Presidente’s Excellence

Sometimes it takes a while to hit your stride. For El Presidente, it took until he was 36. That's when he earned his first All-Star selection. He would go on to earn a total of four in his career. All of them came in the 1990s.

There's also that one magical game in 1991 where he was absolutely perfect. That season ended up being his best as well as he led all of baseball with a 2.39 ERA.

Dennis Martinez — Career	Total
W	245
L	193
ERA	3.70
G	692
IP	3999.2
SO	2149
WHIP	1.27
SV	8
All-Star selections	4

10. Curt Schilling: The Big Game Performer

It is a wonder how Curt Schilling is not in the Hall of Fame. He was one of the icons of the 1990s on the mound. That legend only grew bigger in the following decade. Even when his teams struggled, Schilling shined. He led the league with 300 strikeouts or more in back-to-back seasons.

He also led the league in WHIP and hits per nine in 1992. Somehow, he never won a Cy Young Award, but that's probably because the competition was incredibly high.

Curt Schilling — Career	Total
W	216
L	146
ERA	3.46
G	569
IP	3261.0
SO	3116
WHIP	1.14
SV	22
All-Star selections	6
World Series titles	3

9. Mike Mussina: The Scholarly Strikeout Artist

Since he came from Stanford, I'm sure Mike Mussina got some jokes said his way in the clubhouse. But there were no jokes being said when he was out on the field. He became one of the iconic aces in the shining history of Orioles rotations.

His ability to induce ground balls also helped him become well known for his glove. He won seven Gold Gloves in his career, showcasing his agility on the mound.

Mike Mussina — Career	Total
W	270
L	153
ERA	3.68
G	537
IP	3562.2
SO	2813
WHIP	1.19
SV	0
All-Star selections	5
Gold Gloves	7

8. Kevin Brown: The $105 Million Man

$100 million dollars seems like a floor standard for any star in today's game. Back then, it was unheard of. You would think that the first player to ever break that threshold was one of the best in the game. You actually would be right.

Kevin Brown had one of the greatest three-year stretches of all time. In 1996, he had an MLB-leading 1.89 ERA and 215 strikeouts. He followed that up with a 2.69 ERA in 1997, when he led the Marlins to a World Series championship. He finished it off with his highest WAR season in 1998 with 8.6. Just amazing numbers for the time and valid reasons to have him break the $100 million barrier.

Kevin Brown — Career	Total
W	211
L	144
ERA	3.28
G	486
IP	3256.1
SO	2397
WHIP	1.22
SV	0
All-Star selections	6
World Series titles	1

7. David Cone: Mr. Perfect’s Journey

David Cone was quietly one of the best pitchers of this decade, even though his name doesn't come up as often as some of his contemporaries. Part of the reason is that he bounced around a little bit in this decade. He was with the Mets to start the decade, where he led all of baseball in strikeouts twice; then he got traded to Toronto, where he stayed for half a season.

After that, he went to Kansas City, where he won his one and only Cy Young Award. Only after that did he go back to Toronto before being traded to the New York Yankees, where many of us remember him.

David Cone — Career	Total
W	194
L	126
ERA	3.47
G	450
IP	2898.2
SO	2668
WHIP	1.26
SV	1
Cy Young	1
All-Star selections	5
World Series titles	5

6. John Smoltz: From Starter to Closer and Back

When you talk about getting the job done for the team, you talk about John Smoltz. He had electric stuff that he had a hard time controlling at first. But when he mastered the command of his pitchers, he was basically unhittable.

Speaking of hits, he even got some hits himself, as he won a Silver Slugger in 1997, something that I'm sure he is even more proud of than his Cy Young Award.

5. Tom Glavine: Master of the Outside Corner

Tom Glavine was simply one of the coolest lefties to watch pitch during his time. Like his Hall of Fame teammate, Greg Maddux, Glavine wasn't exactly overpowering hitters.

He didn't have to fight fire with fire. He fought fire with water as he used great command and great pitch selection to become one of the great pitchers of this era.

Tom Glavine — Career	Total
W	305
L	203
ERA	3.54
G	682
IP	4413.1
SO	2607
WHIP	1.31
SV	0
Cy Young	2
All-Star selections	10
Silver Sluggers	4
World Series titles	1

4. Pedro Martinez: The Fearless Dominican Dynamo

I don't think it gets talked about enough how inspirational Pedro Martinez was throughout his legendary career. He inspired so many kids from so many different backgrounds to pitch with no fear and with great confidence.

It wasn't just the fact that he was from the Dominican Republic and inspired so many kids from that country. It was also the fact that he was called too skinny back when he was with the Dodgers and simply developed into one of the strongest pitchers in baseball. It's an underdog story that has a mountaintop finish.

Pedro Martínez — Career	Total
W	219
L	100
ERA	2.93
G	476
IP	2827.1
SO	3154
WHIP	1.05
SV	3
Cy Young	3
All-Star selections	8
World Series titles	1

3. Randy Johnson: The Big Unit’s Intimidation Factor

The Big Unit was a big problem for opposing hitters throughout the 1990s. It's cool that you can kind of watch his journey to becoming one of the greatest of all time through this decade. He went from a wild flamethrower to a masterful ace.

He led the league in strikeouts for four straight seasons and gave the city of Seattle a ton of hope. Two of his five career Cy Young Awards came in this decade as this Hall of Famer got better with age.

Randy Johnson — Career	Total
W	303
L	166
ERA	3.29
G	618
IP	4135.1
SO	4875
WHIP	1.17
SV	2
Cy Young	5
All-Star selections	10
World Series titles	1

2. Roger Clemens: The Rocket’s Dominance

There is no more accomplished pitcher than Roger Clemens. I know we talked about the use of steroids in this era at the top of this article, so it can't be ignored that he is one of the more well-known cases of using them as a pitcher. That being said, he was utterly dominant throughout this decade, winning three Cy Young Awards and earning the ERA title five times.

Roger Clemens — Career	Total
W	354
L	184
ERA	3.12
G	709
IP	4916.2
SO	4672
WHIP	1.17
SV	0
MVP	1
Cy Young	7
All-Star selections	11
World Series titles	2

1. Greg Maddux: The Professor’s Perfect Control

Greg Maddux didn't just get wins with his arm. He got wins with his brain. Dominance doesn't have to come with a 100mph fastball. With The Professor, dominance comes through changing speeds and tunneling pitches.

One of my favorite unofficial stats is "the Maddux," where a pitcher can get a complete-game shutout under 100 pitches. That is something that even today's managers would love to see.

Greg Maddux — Career	Total
W	355
L	227
ERA	3.16
G	744
IP	5008.1
SO	3371
WHIP	1.14
SV	0
Cy Young	4
All-Star selections	8
Gold Gloves	18
World Series titles	1

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