Baltimore Orioles History: Top 5 Orioles All-Time Leaders in Wins

5 Oct 1997: Pitcher Mike Mussina of the Baltimore Orioles throws the ball during a game against the Seattle Mariners at Camden Yards in Baltimore, Maryland. The Orioles won the game, 3-1.
5 Oct 1997: Pitcher Mike Mussina of the Baltimore Orioles throws the ball during a game against the Seattle Mariners at Camden Yards in Baltimore, Maryland. The Orioles won the game, 3-1. /
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The Baltimore Orioles have had plenty of exceptional starting pitchers throughout their franchise’s history. Here, we’ll take a look at the Orioles top five all-time win leaders.

The Baltimore Orioles history includes a group of remarkable pitchers, which led to the Orioles glory days of World Series titles. In this edition of Orioles all-time lists, we highlight the top five most winningest pitchers in Orioles history.

The five pitchers earned a long list of accomplishments throughout their careers and as a group, they combine for five Cy Young awards, 19 All-Star selections, all own World Series rings (except for Mussina), 11 Gold Gloves, and much more.

Most noteworthy, the group of pitchers below was all 20-game winners multiple times throughout their career. The last time an Orioles pitcher won 20 games in a single season was 34 years ago when Mike Boddicker went 20-11 in the 1984 Orioles season.

Here are the top five all-time win leaders in Orioles history, as well as highlights throughout their memorable Orioles career.

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5. Mike Flanagan, 141 Wins

For over a decade, legendary pitcher Mike Flanagan spearheaded the Baltimore Orioles starting rotation, including two World Series titles and named AL Cy Young Award Winner in 1979.

Flanagan’s memorable Orioles career began in 1971 as the Orioles selected him in round No. 7 of the 1973 MLB draft. Two years later, Flanagan made his MLB debut on Sept. 5, 1975, against American League East division rival New York Yankees.

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The Orioles lefty recorded his first ever complete game shutout in the Orioles’ 2-0 victory over the Oakland Athletics during the 1977 season. However, Only did we know that it was the outset of Flanagan’s 1978 and 1979 seasons proved to be the best years of his storied 15-year career in Baltimore.

First, in 1978, Flanagan made a career-high 40 starts and went 19-15 with a 4.03 ERA. Orioles manager Earl Weaver was confident about Flanagan’s abilities and gave him the Opening Day start with a rotation featuring Jim Palmer, Scott McGregor and Dennis Martinez.

The year after, Flanagan won a career-best 23 games with a 3.08 ERA to help the Orioles advance to the 1979 World Series against the Pittsburgh Pirates. The Orioles were unable to secure a World Series title that season, but eventually got his deserving World Series ring in 1983.

Flanagan was named 1979 Cy Young and outdueled Tommy John, Ron Guidry, Jim Kern, among others Strangely, Flanagan didn’t earn an All-Star spot during his 1979 Cy Young season. How does that happen?