Most Cy Young Awards Won

Roger Clemens holds the record for the most Cy Young Awards, with seven, won between 1986 and 2004. No other pitcher has more than five, and Clemens collected his across four different teams over nearly two decades, a testament to sustained excellence at the game’s most demanding position.

The Cy Young Award is baseball’s top pitching honor, given each season to the best pitcher in each league. Winning it once marks an ace; winning it repeatedly separates the truly historic arms from the merely great. Here is the full leaderboard of the sport’s most decorated pitchers, the careers behind the numbers, and who could climb it next. All figures are as of the 2025 season.

The record holder: Roger Clemens and seven awards

Clemens won his first Cy Young in 1986 with the Boston Red Sox and his last in 2004 with the Houston Astros, an 18-year span that touched four franchises. His combination of overpowering velocity and fierce competitiveness allowed him to reinvent himself repeatedly and remain elite deep into his 40s.

That longevity is the essence of the record. Winning seven Cy Youngs requires not just a dominant peak but the durability to stay at the top across generations of hitters, and no pitcher has matched what Clemens achieved.

The full leaderboard of Cy Young winners

The table below ranks pitchers by total Cy Young Awards. Active players are noted.

Rank	Awards	Pitcher	Award years
1	7	Roger Clemens	1986, 1987, 1991, 1997, 1998, 2001, 2004
2	5	Randy Johnson	1995, 1999, 2000, 2001, 2002
3	4	Steve Carlton	1972, 1977, 1980, 1982
3	4	Greg Maddux	1992, 1993, 1994, 1995
5	3	Sandy Koufax	1963, 1965, 1966
5	3	Jim Palmer	1973, 1975, 1976
5	3	Tom Seaver	1969, 1973, 1975
5	3	Pedro Martinez	1997, 1999, 2000
5	3	Clayton Kershaw*	2011, 2013, 2014
5	3	Max Scherzer*	2013, 2016, 2017

*Clayton Kershaw and Max Scherzer are active; their totals are current through the 2025 season. Justin Verlander, also active, has three as well (2011, 2019, 2022).

The list spans the award’s entire history, from Sandy Koufax and Tom Seaver to modern aces, but Clemens’s seven and Randy Johnson’s five sit clearly ahead of the pack.

Randy Johnson, Maddux and the four-time winners

Randy Johnson’s five awards, including four straight with Arizona from 1999 to 2002, make him the closest challenger to Clemens. Steve Carlton and Greg Maddux follow with four each, Maddux famously winning his in four consecutive seasons. Maddux’s control-driven brilliance, built on a low earned run average across many years, connects to the fundamentals explained in our guide to ERA in baseball.

The active chase

Among the many three-time winners, Clayton Kershaw, Max Scherzer and Justin Verlander are all still pitching, giving them a theoretical path toward the top of the list. Each would need a remarkable late-career run to approach Clemens, however. These aces already rank among the greatest baseball players of their generation, and their honors sit alongside the hitting distinctions on our most MLB MVP awards leaderboard.

Why the record matters

The Cy Young rewards the pitcher who most dominates a season, and stacking them up demands both a towering peak and rare durability. Clemens’s seven, earned across four teams and nearly 20 years, is the definitive measure of pitching greatness. With the modern game leaning on pitch counts and shorter starts, sustaining that level long enough to challenge the record is harder than ever.

The short version: Roger Clemens holds the Cy Young record with seven awards, ahead of Randy Johnson (5) and the four-time winners Steve Carlton and Greg Maddux. As of the 2025 season, active aces Clayton Kershaw, Max Scherzer and Justin Verlander lead the chase with three apiece, but Clemens’s seven still stands alone.