The Cubs have played 2,595 regular-season games against the Pirates, 95 more than against any other opponent.
They have lost 39 more than they have won, 1,269 to 1,308 (18 games were ties) despite outscoring the Pirates by 521 runs.
Each team has dominated the rivalry at times.
Most recently, it has been the Cubs. Since 2015, they are 96-59 and have won the season series every year.
From 2001-12, the Cubs were 113-83 and lost the series only twice.
On the other hand, from 1969-94, they were only 183-265.
In all, the Cubs have won the series 56 times and lost it 60. They have split 21.
In 2023, the Cubs finished 10-3 against the Pirates. That tied for their fewest losses against them in the Modern Era. They were 8-3 in 1998.
They also lost 3 times in 1890 -- and won 17.
BEFORE THEY WERE PIRATES
The Cubs have been a member of the National League since its creation, in 1876.
The only other survivor are the Braves, who started as the Boston Reds or Red Stockings.
Today's Pirates were known as Allegheny City or the Alleghenys when they began play in 1882, as 1 of 6 teams that comprised the rival American Association. They finished 39-39, good for fourth place.
They tumbled to 31-67 in their second season, then to 30-78-2 in their third.
But after going 56-55 and 80-57-3 in the next 2, the Alleghenys were invited to join the National League, and quickly accepted.
They had finished second in their final season in the AA. In the NL, between 1887 and 1889, they came in sixth twice, then fifth, at 61-71-2.
After the 1889 season, a new league was formed: the Players League, aka the Brotherhood.
As its name suggests, it was organized by the players, in a revolt against the reserve clause and other restrictive practices of the NL and AA.
A huge number of players jumped to the new league, and the Alleghenys were among the hardest hit by defections.
Of their 13 position players in 1889, only 3 returned in 1890: Billy Sunday, the famous outfielder/evangelist; George "Fog Horn" Miller, who switched from catcher to third base; and second baseman Fred Dunlap, who would play only 17 games, compared to 121 the previous year.
The only returnee among 11 pitchers was 25-year-old Bill Sowders, who had gone 6-5 in 13 games, 11 of them starts, after being purchased from Boston in late July.
Gone were 33-year-old Pud Galvin, a future Hall of Fame, who in 1889 had won 23 games, his 10th season with at least 20.
Harry Staley, 22, had departed as well, after having won 21 games -- and leading the league in losses, with 26.
The patched-together club began the season with a 3-2 win at home over Cleveland, then beat Spiders in 2 of the next 3 games as well, the last by 20-12.
They won, then lost, against Cincinnati, making their record 4-2 on April 28, as they embarked on a 25-game, 7-city road trip.
They lost 3 straight at Chicago to the Cubs, then known as the Colts, won the series finale, tied at Cleveland, then dropped 4 in a row.
After 2 wins at Cincinnati and a split of the first 2 games at Brooklyn, the Alleghenys were 8-10-1 and just 3.5 games out of first.
They never came closer to .500 the rest of the season.
An 18-2 shellacking began an 11-game losing streak that continued until the last game of the road trip, when they won at Boston, 9-8.
Upon returning home, the Alleghenys lost 3 times to the Colts.
And then they headed out of town once more.
Why so soon? Because attendance at their games in Pittsburgh was so low that other NL teams started refusing to play there, saying it cost them more to make the visit than they received as their share of the gate receipts.
Beginning with 3 games moved to Cincinnati, June 5-7, the Alleghenys would relocate 26 games: 22 to rival parks and 1 each to Canton, Ohio, and Wheeling, W. Va.
From July 5 to Sept. 17, the Alleghenys played 58 of 66 games on the road; for the season, 98 of 138.
They closed out September with 10 games at home, for a total of 40 all year, which were viewed by 16,064 fans -- 402 per game. One of the final 10 attracted no more than 100.
The Alleghenys' last 2 games were relocated to Brooklyn, where they lost, 9-1 and 10-4.
Those defeats made them 15-103-1 since their 8-10-1 start, for a final record 23-113-2 and a winning percentage of .174.
That was barely half the .331 of the next-worst team in the league, the Spiders (44-88-4).
Champion Brooklyn was almost 500 percentage points better than the Alleghenys, at .667 (86-43).
The Alleghenys trailed the Bridegrooms by 66.5 games. They even trailed the Spiders by 23.
JUST 2 TEAMS WORSE
How bad is a .174 winning percentage?
Only 2 National League teams ever have had a lower one.
The Cincinnati Reds were .138 (9-56) in 1876, the league's first season.
The Cleveland Spiders were .130 (20-134) in 1899, when their new owners kept sending virtually every able-bodied player to St. Louis, which they also owned.
Those Spiders also had their home games boycotted by rival teams and wound up playing 112 games on the road.
The worst percentage since the Spiders' .130 was .237 by the 1916 Athletics (36-117-1).
Only 2 subsequent teams have won no more than one quarter of their games: the 1935 Braves (.248, 38-115) and 1962 Mets (.250, 40-120).
In the last 6 decades, the 2003 Tigers had the worst percentage, .265 (43-119).
The awful 2023 Athletics were .309 (50-112).
The Cubs' worst ever was .364, when they went 59-103 in 1962 and again in 1966.
PARADE OF PITCHERS
Back in 1890, the Alleghenys used 20 pitchers. Only 1 had a winning record: Henry Jones, 2-1.
8 pitchers had decisions without winning a game, including 2 who were 0-6 and another who was 0-5.
5 more won just once, led by Bill Phillips and "Crazy" Schmit, both 1-9.
Billy Gumbert managed to go 4-6. Kirtly Baker was 3-19, with 2 of the team's 3 shutouts.
Bill Sowders was 3-8; Dave Anderson, 2-11; and Guy Hecker, 2-9.
They combined to give up 1,235 runs -- 8.95 per game -- while averaging 11.9 hits and 4.4 walks per 9 innings.
They walked 573 and struck out 381.
The team ranked last in runs, earned runs, hits, home runs and ERA.
The offense, meanwhile, was last in all three components of the slash line, with .230/300/.294, for an OPS of .594.
The 7 other teams combined were .257/.333/.349, .682.
The Alleghenys scored 597 runs, an average of 4.33, so they were outscored by 4.62, more than twice as many.
As they slogged through their wretched season, the Alleghenys were a constant target of derision in the press, much like the first-year National Hockey League team that went 8-67-5 in 1974-75.
One of their 3 head coaches remarked at one point that he sometimes forgot the team was based in Washington, since the media so often called them "the hapless Capitals."
A Chicago newspaper, the Inter Ocean, was especially disdainful of the 1890 Alleghenys.
Here are a few excerpts from its coverage of some late-season games between the Alleghenys and the Colts, whose 17-3 domination of the series helped them to finish 83-53-3, in second place, 6.5 games behind Brooklyn.
Dates are those on which the games were played. The newspaper stories appeared the next day.
At the time, the Pittsburgh's name was spelled without the final "h."
Some paragraph breaks have been added for easier reading.
AUG. 16: COLTS 18, ALLEGHENYS 5
The Pittsburg club of the National League has no license to live.
It is the most foul smelling mistake that a great league has ever numbered among its children.
Two, or possibly three, of [owner] Palmer O'Neil's men are ball players; the balance would be more in harmony with the conditions if they would go back to planting corn.
One man looms up among the lot like a pair of yellow shoes. Fog Horn Miller is a ball player from breakfast until the cows come home. He deserves a better fate.
It was almost pathetic, yesterday's exhibition. Nine men with Pittsburg uniforms playing a game in which they had no more hope of winning than you have of falling heir to a million.
But they made a sort of half-hearted bluff at it, and old man Miller roared at the coacher's line just as though the whole thing was serious, and not a monstrous joke.
In the fifth inning, when the Colts limbered up and did nothing but run around the bases and smash the ball, until thirteen men had scored, the Alleghenys didn't seem to mind it much. They only shrugged their shoulders and glances at the crowd with a weary look, as though to say:
"Bless you, don't worry about us; we can stand it, we're used to it. That's nothing to what you would see if you traveled with us right along."
They put up a fat-headed young man named Phillips to pitch. J. Palmer tosses a coin every morning to see who will pitch in the afternoon.
There are only nine men traveling with the Pittsburg flag nowadays. Frost is coming, and J. Palmer wants to put a little something by for Christmas gifts and the winter's coal.
So they take turns at pitching. Mr. Phillips doesn't know much about the business yet, but he will get there all right, in time. There must be absolutely no restriction as to the time.
In only two innings did the Chicagos score at all. In only two innings did they care to wear out their shoes. Five at one clip and thirteen in another were all they wanted.
AUG. 18: COLTS 9, ALLEGHENYS 3
If the Pittsburgs were to hang out here the balance of the summer, Captain Adrian Constantine would become a merry, light-hearted boy again.
Yesterday he loped around the grounds and jumped up and down like a calf in a meadow. He is smiling so much lately that he is getting holes in his cheeks, and he occasionally stops to exchange anecdotes with low people in the bleachers, as though to show he wasn't proud, and was too magnificent to be selfish.
The Colts won again, of course. No one had any idea they wouldn't. Even the Pittsburgs were sure of of it, and played like trained seals.
Some of the people in the grand stand enjoyed it, though, just as they might have enjoyed a sacrifice of Christians in a Roman arena.
Sir Guy De Montefort Hecker pitched, or made a bluff at it. But an awful sense of the mutability of time steals over one who sees Guy pitch. Mr. Hecker is always a day-before-yesterday pitcher.
AUG. 19: COLTS 7-18, ALLEGHENYS 4-3
The Pittsburgs and Mr. Anson's men played two games. Mr. Anson's men won both, a fact not so startling as to cause many people afflicted with heart disease to drop dead.
If there ever were a bald-headed misfit on earth it is the Pittsburg club, and it is perhaps one of the most exasperating evils of the merry baseball war that this barn-storming combination of lunch counter clerks is permitted to roam through the country destroying the public peace of mind.
The first game had a pleasing variation of the usual kind, inasmuch as the Colts didn't get on a good head of steam until the sixth inning, thereby causing a faint, trembling hope in the Pittsburg breast that they might, through some strange chance, win a game. . . .
The second game would have been equally stupid for the chilled people scattered like pins in a cushion through the stand had it not been for the introduction of a novelty.
The novelty was a stray pitcher whom the Pittsburgs heartlessly stuck in the box in the seventh inning, for aliens to make a plaything and a toy.
The pitcher's name was Hayner, and the only things he seemed to lack was the ability to pitch and bat. Otherwise he appeared to be doing quite well.
SEPT. 8: COLTS 7, ALLEGHENYS 3
Jay Palmer O'Neil's Folly Company dropped in at Mr. Anson's slaughter-house yesterday.
People in this nervous, care-cankered world, who fidget down life's baseball line a-wailing and a-gnashing their teeth at the slings and arrows of outrageous fortune, should read a lesson from the Pittsburgs.
Day after day they picked their way along a desolate and stony path, without reward, with never a friendly word to brighten the way.
When they arise the morning grim Defeat stares them in the face; when they sink to rest at night grisly Misfortune with flaming eyes sits at their feet.
But do they moan, and wring their hands, and curse mankind? No, they plod on, patiently and uncomplainingly. With a load that daily grows heavier and heavier heaped on their shoulders, and the world pitilessly hurling coarse gibes and jests after them, they only sigh, and sometimes almost smile.
Fortitude and Christian resignation can go no further.
Yesterday they marched onto the League grounds to get their daily installment of puree like the martyrs in the old pictures, serene and undaunted, with fiery death coming in on the next car.
They knew they had no more show of winning than grandma has in a hurdle race, but they put on their faded suits and marched out like men going to a fete.
And when their toil was over they put on their coats like hired men who know they have done a good day's work and deserve a good supper when they get to the house.
The game as a contest was featureless. There was no extraordinary fielding, no heavy hitting.
There was no necessity for it.
SEPT 9: COLTS 12, ALLEGHENYS 4
The Chicago were out for practice again yesterday. It was not a good day for it either, being chilly and stuffed with gloom, but the Pittsburgs wanted their guarantee for railroad fare and laundry bills, so the good, kind Captain rolled up the curtain and shouted, "On with the farce."
It was desolate day for ball; a bleak wind chased up and down the barren grand stand, and reporters in the boxes above had icicles in their whiskers.
The contest was in harmony with the weather. Not a glimmer of enthusiasm appeared through the entire game, and the half-frozen people in the stand were as solemn visaged as homeless orphans.
There was was something cruel in their faces, as one imagines the solid citizens of Rome must have looked when they were enjoying a first-class massacre in the arena.
In this case the massacre of the Friendless by Captain Anson and his hired vassals was short, sharp and terrible. Pittsburg hadn't the faintest glint of hope at any stage. They fielded like a blind man playing pool, and their bluff at the bat was a hollow-eyed mockery.
Hutchison pitched like a fond father playing bean bag with his youngest, and still the Ghosts got but four hits.
Sales, who is to have been a good shortstop once, probably in the Tertiary Age, made five errors.
SEPT. 10: COLTS 8, ALLEGHENYS 1
The nine cankers on the face of the National Game have departed.
Like Hawthorne's wanderer groping hopelessly down the years after the Unpardonable Sin, they went silently out again into the night, the phantoms of a vanished hope.
As the bus rolled down Dearborn Street to the depot, people paused as a chance ray of light fell onto the nine cowering forms within, to gaze in sorrow at the spectacle.
Nine men with hungry eyes, who said no word and started at every sound, into whose breasts seemed to have burned the damnable scarlet letters of their trade, withering in their hearts all that was glad and good in life.
Chicago can breathe easier this morning. The homeless specters have gone, and they will never, never come back to us.
No affidavits will be required as to who won yesterday. But if the Pittsburgs, by some wild whim of Fortune, had won the coroner would have had employment at the league grounds far into the night.
As it was the game was as full of excitements as a paving-stone is full of wind.
The brave souls who speckled the grand stand never opened their faces except now and then to unload a low laugh of scorn on the Allies, and no one seemed to take an active interest in the game except an industrious painter, working by the day in an empty house across the street.
Singularly, the industrious painter began on the front windows when game was called [i.e., begun]. The painter watched the game, and the crowd watched the painter.
Pools were opened in Section A on the industrious painter -- working by the day -- finishing one window before the sixth inning. But he weakened on the upper sash, and the misguided upholders of the dignity of labor gave up their gold.
Details of the game area almost superfluous, it was such a lob-sided [sic], milk-and-water affair. . . . The Colts hammered out base hits and doubles and triples right merrily. . . .
Now that the Clevelands are among us we may see some ball-playing. It can't be worse, and may be a great dealt better.
With an infusion of new players thanks to the demise of the Players League, the Alleghenys improved to 55-80-2 in 1891, then enjoyed back-to-back winning seasons. Their 81-48-2 mark in 1893 left them second, just 5 games out of first.
Several mediocre seasons followed.
After 1899, the NL expelled 4 teams, including the Louisville. Its owner took over Pittsburgh, now known as the Pirates, and brought with him most of the Colonels' top players, led by Honus Wagner.
They finished second in 1900, then won 3 straight pennants. In 1909, they won another, going 1109-42-2 to beat out the 104-49-2 Cubs, then won the World Series.
The Pirates have won the Series 4 more times since then, most recently in 1979. They went 12-6 that year against the Cubs.