The Best Pittsburgh Pirates Seasons and Every October Run

By 4Baseball Staff · · 11 min read

Pittsburgh's best seasons ranked by winning percentage, plus all 20 postseason series the Pirates have played, from the first World Series in 1903 to the 2015 wild-card game, grouped by era.

The Pittsburgh Pirates have won five World Series, and they have never lost one since 1927. That is the strangest fact in the club's postseason ledger. Seven times the Pirates have reached the World Series, and the five titles in 1909, 1925, 1960, 1971 and 1979 each ended 4-3 in the Pirates' favour, every one of them a series that went the distance. Then there is the other half of the ledger. The same franchise has lost seven of nine National League Championship Series, and it has not won a postseason series since a single wild-card game in 2013.

This article goes through the Pirates' best regular seasons by winning percentage and then through every one of the 20 postseason series in the historical record, in order, grouped by era. It is a story with several high points, two long droughts, and a run of near-misses against one opponent in particular. Where the database does not carry a number, the article does not guess at it.

Pittsburgh Pirates82-80 · NL Central

For the full franchise story, the history of the Pittsburgh Pirates covers each era, and the best players in Pirates history covers the people. This piece sticks to seasons and series.

The six best seasons by winning percentage

Among Pirates seasons of 100 or more games, six rank highest by winning percentage. Percentage is the fair measure because schedules changed from about 130 games in the 1890s to 154 and then 162.

Season Record Win pct Finish Result
1902 103-36 .741 First Pennant
1909 110-42 .724 First World Series champions
1903 91-49 .650 First Pennant, lost World Series
1901 90-49 .647 First Pennant
1908 98-56 .636 Second None
1893 81-48 .628 Second None

The list is unusual because it is almost entirely a product of the first decade of the twentieth century. Not one of the six comes after 1909, even though the club won four more World Series after that year. The Pirates' later champions won pennants with records in the mid-90s, not the low .700s: the 1925 team went 95-58, the 1960 team 95-59, the 1971 team 97-65 and the 1979 team 98-64. They were very good, not dominant.

The most wins in a season is the 1909 total of 110, which is also the club's most wins in any year. The other side of the ledger is just as stark. The five worst seasons in the database are 1890 (23-113), 1952 (42-112), 1884 (30-78), 1953 (50-104) and 1917 (51-103). The 1952 team lost 112 games, and only the 1890 team, which lost many players to the short-lived Players' League, has a worse record in that list.

1882 to 1900: the Alleghenys learn to win

The franchise started in 1882 as the Alleghenys, listed in the database under the spelling Pittsburg, and became the Pirates in 1891. The team's early years were hard. The 1884 club went 30-78 and the 1890 club went 23-113, the worst record in the club's history.

The first great season came in 1893, when the club went 81-48 and finished second. It did not win a pennant, but it showed the Pirates could compete. The club's first manager of lasting note, Fred Clarke, arrived in 1900, and he is the most important figure in the first half of the club's story. Clarke managed Pittsburgh from 1900 to 1915 and went 1,422-969 in 2,427 games, both the most games and the most wins of any manager in the club's history.

Clarke's teams were built around Honus Wagner, who played for the club from 1900 to 1917 and collected 2,967 hits and 639 stolen bases while doing it. Wagner's career is a topic by itself; here it is enough to say that Pittsburgh had the best shortstop in the game at the same time as it had the best team in the league, and those two facts were connected.

1901 to 1903: three pennants and the first modern World Series

The Pirates won the National League in 1901, 1902 and 1903. The 1901 club went 90-49. The 1902 club went 103-36, the best winning percentage in club history at .741, and led the league. The 1903 club went 91-49 and won a third straight pennant.

There was no World Series in 1901 or 1902. The National League and the new American League were still at war, and the two sides did not meet in a championship series until 1903. When they finally did, the Pirates were there. Boston of the American League won the first modern World Series five games to three, in a best-of-nine format. The Pirates' 3-5 loss is the first entry in the club's postseason ledger.

This is a good place to be honest about what the record shows and what it does not. The historical record tells us the result and the games won and lost by each side. It does not tell us why Pittsburgh lost, and any detailed account of the 1903 series belongs to the sources that cover it game by game. What the numbers do show is that the Pirates had the best record in the league three years running and came out of those three years with a single series loss. For the structure of the early Series, see the history of the World Series.

1908 and 1909: the near-miss and the first title

In 1908 the Pirates went 98-56 and finished second, one game behind the Cubs, one of the best records in the club's history to miss a pennant. The National League race that year was settled only after the regular season by a replayed game between the Giants and the Cubs, and Pittsburgh was one of the three clubs in the chase. A 98-win team went home without a pennant, which tells you how tight the race was.

The next year the Pirates made no mistake. The 1909 team went 110-42 for a winning percentage of .724, the second best on the list above, and it opened a new ballpark, Forbes Field, in the course of the year. Forbes Field would be the club's home for six decades, and the 1909 attendance of 534,950 was a club record at the time.

The 1909 World Series pitted Pittsburgh against Detroit, which had Ty Cobb, and it went seven games. The Pirates won, 4-3. It was the club's first championship, and it is the one that put Wagner and Cobb in the same story, one batting champion against another, in a final that went the distance. The all-time greats article puts Wagner in the context of the other Pirates stars.

1925 and 1927: a comeback and a sweep

The Pirates won two more pennants in the 1920s. In 1925 the club went 95-58 and met the Washington Senators, the franchise that later became the Minnesota Twins, in the World Series. Pittsburgh trailed three games to one and won the last three, taking the Series 4-3. They would pull off the same comeback again in 1979.

Two years later, in 1927, the club went 94-60 and won the pennant behind the Waner brothers. Paul Waner won the National League Most Valuable Player award that year, and his brother Lloyd was in his first season in the majors. Pittsburgh then met the Yankees in a World Series that is usually remembered for the strength of the Yankee lineup, and lost four games to none.

The 1927 sweep is the last World Series the Pirates have lost. That is a remarkable record in its own right: the club's three finals after 1927 all ended in titles. But the bigger story of the next three decades was not October. The Pirates did not win another pennant until 1960, and during that gap they had some of the worst seasons in club history. The 1952 team went 42-112, the 1953 team 50-104, and the franchise that had won two World Series in the 1920s was one of the weakest in the league by the middle of the century.

1960: Mazeroski and the Yankees

The 1960 Pirates went 95-59, won the National League, and met the New York Yankees in the World Series. Danny Murtaugh was the manager. Murtaugh went 1,115-950 in 2,068 games across several stints from 1957 to 1976, and he was in the dugout for both the 1960 and 1971 titles.

The Series is famous for a strange statistical profile. The Yankees outscored Pittsburgh by a wide margin over the seven games, winning three of them by lopsided scores, but the Pirates won the four close ones. The finale, Game 7, was decided by a home run by Bill Mazeroski leading off the bottom of the ninth. It remains the only World Series to end on a home run in the seventh game, and Mazeroski, who played 17 seasons for the club and collected 2,016 hits, is in the Hall of Fame.

The 1960 team collected the awards as well. Dick Groat won the National League MVP, and Vern Law won the Cy Young Award, which in that year was given to one pitcher for both leagues combined. Law's 162 wins for the club rank sixth in club history.

1970 to 1979: the Reds in the way, then two more titles

The 1970s were the best decade in the club's history, and the Pirates finished first in the National League East in 1970, 1971, 1972, 1974, 1975 and 1979. The division format meant a League Championship Series, and there the Pirates found the same obstacle year after year: the Cincinnati Reds.

Year Pirates NLCS result World Series
1970 89-73 Lost to Cincinnati, 0-3 none
1971 97-65 Beat San Francisco, 3-1 Beat Baltimore, 4-3
1972 96-59 Lost to Cincinnati, 2-3 none
1974 88-74 Lost to Los Angeles, 1-3 none
1975 92-69 Lost to Cincinnati, 0-3 none
1979 98-64 Beat Cincinnati, 3-0 Beat Baltimore, 4-3

In 1971 the Pirates beat the Giants in the NLCS and then met the Orioles in a World Series that went to seven games. Baltimore won the first two games, and Pittsburgh took four of the last five. Roberto Clemente was named the Series most valuable player, and Steve Blass pitched a complete game in Game 7. A few weeks earlier, on September 1, the club had fielded the first lineup in major-league history made up entirely of Black and Latin American players, a moment now widely documented.

The 1972 season ended in an NLCS loss to Cincinnati, decided in the bottom of the ninth inning of Game 5 on a wild pitch. It was also Clemente's last season. He collected exactly 3,000 hits for the club before he died in a plane crash on December 31, 1972, on a flight carrying relief supplies to earthquake victims in Nicaragua. His 3,000 hits and 240 home runs, and his .317 average in the club's sheet, are the numbers; the rest is a life that went beyond them.

The 1979 team, which adopted the disco hit We Are Family as its anthem, went 98-64 and swept Cincinnati in the NLCS, 3-0. It then fell behind Baltimore three games to one in the World Series and won the last three, finishing 4-3. Willie Stargell, who hit 475 home runs for the club, shared the National League MVP award that year and was the most valuable player of both the NLCS and the World Series. Chuck Tanner managed the club to the title. The Reds' own record in these same series shows the mirror image of the Pirates' decade.

1990 to 1992: three division titles and a ninth-inning loss

After a decade without a title, the Pirates returned to the top of the National League East in 1990 under Jim Leyland. The team went 95-67 in 1990, 98-64 in 1991 and 96-66 in 1992, three straight division titles, with Barry Bonds winning the MVP award in 1990 and 1992 and Doug Drabek winning the 1990 Cy Young Award.

None of the three teams reached the World Series. In 1990 the Pirates lost the NLCS to Cincinnati, 4-2. In 1991 and 1992 they lost to Atlanta, both times in seven games, 3-4. The 1992 series ended in one of the best-known endings in postseason history: Pittsburgh led in the ninth inning of Game 7, Atlanta rallied, and Sid Bream scored the winning run on a single by Francisco Cabrera, sliding home just ahead of the throw.

What followed was worse. Bonds left as a free agent after the 1992 season, and the club began a run of losing seasons that lasted twenty years. The 1993 team went 75-87 and finished fifth, and every season through 2012 produced a losing record. It is among the longest such streaks in North American professional sports. The three NLCS losses are painful partly because of what followed them: a franchise that had played in the NLCS three years running then spent two decades under .500.

2013 to 2015: back in October, three wild cards

The streak ended in 2013 with a 94-68 season under Clint Hurdle, who managed the club from 2011 to 2019 and went 734-719. Andrew McCutchen won the National League MVP award that year, and the club earned a wild-card berth, the first of three in a row.

The Pirates beat Cincinnati in the one-game wild-card round at home, which is the club's most recent postseason series win, and then lost the Division Series to St. Louis, 3-2. In 2014 the club went 88-74 and lost the wild-card game to San Francisco, 0-1, with Madison Bumgarner pitching a shutout. In 2015 the club went 98-64, the best record in the three-year run, finished second in the division behind St. Louis, and lost the wild-card game to the Cubs, 0-1.

The 2015 season also set the club's attendance record, 2,498,596 at PNC Park. Pittsburgh has not been back to the postseason through 2025. The 2025 team went 71-91, though it did have the National League Cy Young Award winner, Paul Skenes, who followed his 2024 Rookie of the Year award with the pitching honour. The PNC Park guide describes the park in which most of this recent history was played.

The scorecard: 20 series, 8 won, 12 lost

Counting every round, the Pirates have played 20 postseason series and have won 8 of them.

Round Series Won Lost
World Series 7 5 2
League Championship Series 9 2 7
Division Series 1 0 1
Wild Card 3 1 2

The split between rounds is the whole story. The Pirates have won five of seven World Series and just two of nine League Championship Series. Their only NLCS wins are the two that led straight to titles, in 1971 and 1979. Every other trip to the NLCS ended with a loss. Four of the seven NLCS losses came against Cincinnati, in 1970, 1972, 1975 and 1990; the other three came against Los Angeles in 1974 and Atlanta in 1991 and 1992.

Put another way: when the Pirates have won the pennant, they have won the World Series in all but two of seven cases. When they have stopped one round short, they have lost close. That asymmetry is partly luck and partly a function of how few teams have made the postseason in the Pirates' history, which makes any small sample misleading.

Common questions

How many World Series have the Pirates won? Five: 1909, 1925, 1960, 1971 and 1979. They lost the 1903 and 1927 finals.

What was the Pirates' best regular season? By wins, 1909, with 110. By winning percentage, 1902 at 103-36 (.741), though 1909 is close at .724.

When did the Pirates last win a postseason series? In 2013, when they beat Cincinnati in the one-game wild-card round. They lost the next round to St. Louis and lost the wild-card game in 2014 and 2015.

Who is the Pirates' all-time home run leader? Willie Stargell, with 475 from 1962 to 1982. Ralph Kiner is second with 301 and Andrew McCutchen is third with 248, through 2025.

Have the Pirates ever finished first in the Central? Not in the database through 2025. The club's three recent berths were wild cards, and its division titles all came in the National League East, in 1970 to 1972, 1974, 1975, 1979 and 1990 to 1992.

Where to go next

The Pirates team page shows the current record and next game, and the PNC Park page lists the dimensions of the club's home since 2001. The Pirates topic page collects news about the team. For the clubs that appear most often in this ledger, read the Reds and Cubs histories.

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