The Cubs’ season came to an end in Milwaukee last Saturday during Game 5 of the NL Division Series.

The Brewers won the NL Central by five games over the Cubs – even though the North Siders won the season series battle and held the tiebreaker – giving them home-field advantage in the winner-take-all game.

The Cubs went 4-1 at home in the postseason, but 0-3 on the road – all in Milwaukee.

“Certainly losing the division put us at a disadvantage in that regard,” Cubs president of baseball operations Jed Hoyer said on Wednesday. “I think that we had to go up there kind of on short rest in that first game, and I think that hurt us.”

[WATCH: Jed Hoyer’s full end-of-season press conference on the Marquee Sports Network App]

Over the course of 162 games, teams will win games they’re supposed to lose, and lose games they’re meant to win.

We examined five games from the 2025 regular season that the Cubs would like to have back, as these games could have impacted their playoff seeding and been the difference between hosting the best-of-five NLDS and potentially still be playing in the postseason.

September 7 vs. Nationals

On a day that celebrated the inductions of Derrek Lee and Sammy Sosa into the Cubs Hall of Fame, the team on the field came up short.

Carson Kelly launched two solo home runs, including one in the 8th inning to give the Cubs a 3-1 lead and a 93.7% chance of winning according to Baseball Savant.

[‘Huge impact’: Cubs president Jed Hoyer weighs in on Kyle Tucker’s free agency]

Daniel Palencia gave up a solo blast to begin the inning to Nationals center fielder Robert Hassell III.

After allowing a single and a walk to CJ Abrams and James Wood, Josh Bell blasted a go-ahead three-run homer to give the Nationals a 5-3 lead. Washington tacked on an insurance run and won the game 6-3.

September 23 vs. Mets

In the final homestand of the season, the Cubs squared off with the Mets as they were fighting to make the postseason.

Cade Horton went three innings before exiting with an injury, but the Cubs were able to secure a 6-1 lead going into the fifth inning, which gave them a win probability of 94.8%.

With two outs in the fifth inning, the Mets scored five runs to tie the game at six.

The big blow came in the eighth inning when Francisco Alvarez hit a two-run home run off Caleb Thielbar to give the Mets a 9-7 lead, a score which held up.

August 2 vs. Orioles

On a day the Cubs honored the late Ryne Sandberg by wearing their blue jerseys at Wrigley Field, Matthew Boyd delivered.

He tossed seven shutout innings, striking out eight while allowing only four hits with no walks.

Entering the eighth inning, the Cubs held a 3-0 lead with their win probability being as high as 96.5%.

With runners on first and second and two outs, the Orioles rallied. Second baseman Jackson Holliday extended the inning with an RBI single, and shortstop Gunnar Henderson launched a three-run blast to give Baltimore a 4-3 lead and the eventual win on the North Side.

May 19 @ Marlins

This was a back-and-forth game that saw the Cubs erase multiple two-run deficits.

The Cubs had a one-run lead with two outs and nobody on base in the bottom of the ninth. At this point, the Cubs had a 95.6% chance of winning.

Marlins center fielder Derek Hill hit a double, and new closer, Palencia, walked the No. 9 hitter on four pitches.

Jésus Sánchez roped a 2-run triple into the right field corner, giving the Marlins an 8-7 win.

March 30 @ Diamondbacks

This was the Cubs’ first series of the regular season on American soil, following the Tokyo Series. After taking two of the first three games, they were primed to win the series.

Kyle Tucker launched a 3-run home run, giving them a 6-2 lead in the eighth inning. At one point after Tucker’s blast, the Cubs had a 96.7% chance to win.

That’s when the wheels fell off.

After a pair of walks to lead off the bottom half, the Diamondbacks went on to score eight runs and win the game, which included an RBI single by relief pitcher Ryne Nelson.

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