Connie Mack chose Chief Bender to start game 1, while Orval Overall was selected by Frank Chance.

Frank Schulte was walked, and it seemed a comeback may be on, but Solly Hofman grounded out, ending the game at 1–4.

[14] Star pitcher Jack Coombs was the starter for the Athletics, while Mordecai Brown began the game for the Cubs.

[22] Jack Coombs started the game shakily, walking Jimmy Sheckard, who was forced out at second after Frank Schulte grounded and got to first base.

Eddie Collins hit a double, allowing Thomas and Lord to reach home and make the score 1–2.

[23] Although Coombs continued to struggle, and twice fumbled the ball in the fifth inning, good fielding allowed Philadelphia to keep Chicago at one run.

[22] Harry Davis singled to left in the bottom of the fifth, allowing Eddie Collins to score from second base, increasing the Athletics' lead to 1–3.

[23] In the seventh inning, the Cubs got one back after Jimmy Sheckard doubled and Frank Chance hit hard to center.

Coombs additionally walked Solly Hofman for the third time, and the game no longer looked as though it was firmly in Philadelphia's hands.

Bris Lord hit a fly-out, but Jimmy Sheckard dropped the ball, and Strunk came home.

Eddie Collins was praised for his performance,[23][24] which involved getting 3 hits out of four at-bats, scoring two runs and batting in another.

[25] An attendance of at least 30,000 fans had been expected by Chicago officials, but only 26,210 people showed up, though those who did stayed almost the entire game in spite of the home team's struggles.

Bris Lord sacrificed, and Home Run Baker singled on a low curveball, putting the Athletics up 1–0.

Chicago quickly matched this as well – Joe Tinker doubled, and Ginger Beaumont and Jimmy Sheckard walked, loading the bases.

With one out and Eddie Collins on first, Home Run Baker hit a triple and put Philadelphia back in the lead.

[25] Chicago's player-manager Frank Chance was ejected from the game, the first time in World Series history that a manager was punished in this way.

The inning started with two outs, and Harry Steinfeldt had the chance to finish it, but he fumbled Home Run Baker's hit and the Philadelphia player got to first.

The bases were filled by Harry Davis and Danny Murphy, and Jack Barry hit his third double of the game to earn the Athletics two runs.

Ty Cobb predicted that they would sweep the series,[27] and Connie Mack confidently pronounced that they would defeat the Cubs in game 4.

Chief Bender was chosen to start for Philadelphia, while King Cole was put out for Chicago as the last hope for the Cubs.

Strunk accidentally slid past third base and was tagged out, but Bender was home before him, tying the game at 1.

Chicago pinch hit Johnny Kling for King Cole in their half of the eighth inning, and put Mordecai Brown on the mound for the ninth.

Player-manager Frank Chance came up to bat with one out, and was hit by the first pitch on the finger, but the umpire ruled that he had walked into it.

[28] Jack Coombs started Game 5 for the Athletics, while Mordecai Brown was tasked with keeping the Cubs in contention.

Further, Philadelphia manager Connie Mack opted to start Topsy Hartsel in left field, moving Bris Lord to center rather than Amos Strunk,[8] and also switched catcher Ira Thomas with Jack Lapp.

He made it to third base when Heinie Zimmerman bunted, and scored a tying run on Harry Steinfeldt's hit.

[33][34] The Athletics capitalized on this, with Jack Lapp's fifth inning single allowing Danny Murphy to score from second base.

Harry Davis was walked – Mordecai Brown's first base on balls in Game 5 – and Danny Murphy tripled.

[34] The Cubs scored a run in the bottom of the eighth when Frank Chance singled to send Jimmy Sheckard home.

Jimmy Archer singled, and Johnny Kling emerged to pinch hit for the pitcher, as he did in Game 4.