Diving into the realm of Captain Obvious, but getting off to a good start in the short “Best of 3” game series that is otherwise known as the “MLB Wildcard Series” is imperative if a team has any true aspirations to win the World Series. The top two teams in each league get a bye for this round, meaning that the Tampa Bay Rays and Cleveland Guardians in the American League and the Milwaukee Brewers and Los Angeles Dodgers in the National League are sitting and waiting to see how the next three days play out to determine their courses of action. However, for the teams involved in this round, this becomes even more magnified, and that’s what we are going to examine here. (We’ll start in order of the start times for game one of the series.)

PHILADELPHIA PHILLIES VS. ATLANTA BRAVES

Taking place at Truist Park in Atlanta, the Philadelphia Phillies will be venturing into enemy territory as the Atlanta Braves claimed the National League East division crown and will be hosting this three-game series. Truist Park has been something of a house of horrors for the Philadelphia Phillies since its inception. Philadelphia is seen as the underdog heading into this matchup for a couple of different reasons. Most notably, an NL Cy Young Award candidate in Chris Sale is on the mound for the Braves in game one.

Jesus Luzardo, a quality All-Star in his own right, will be on the mound for game one for the Phillies; he hasn’t pitched much in September due to an injury. The Phillies are also looked at in a less-than-favorable light in the series because of how poorly they limped into the postseason, only securing their entry on the final day of the regular season. Not to mention, their prized trade deadline acquisition of Luis Arraez has been left off the Wildcard Series roster due to suffering a nasty-looking ankle injury. Should the Phillies advance, Arraez’s availability will still be in question. And while Arraez hasn’t been producing at his usual level with the Phillies, he gives the boys from the city of Brotherly Love a different kind of bat in their lineup.

CHICAGO WHITE SOX VS. HOUSTON ASTROS

The American League Wildcard series pitting the Houston Astros against the Chicago White Sox is arguably the most intriguing matchup of all. Simply for no other reason than the fact that the Astros stumbled and defaulted their way into the postseason. Sitting with a regular-season record of 81-81, a .500 ballclub making the postseason seems almost blasphemous, yet that is what we have in 2026. And much like the aforementioned Phillies, the Astros only secured their spot in the final game of the season. However, unlike Philadelphia, Houston also secured their 81st victory in that game as well. If not, we would’ve seen an under .500 team make the postseason. Houston’s claiming of the very weak AL West division crown awards them, however unwarranted, the right to host this three-game series against the White Sox. Chicago, after three straight 100-loss campaigns, made history by making the postseason in 2026. And while slightly disappointed that they just missed out on the AL Central division crown, the postseason entry is prize enough. However, don’t let that fool you; this team is poised to surprise people in the postseason.

BOSTON RED SOX VS. NEW YORK YANKEES

The best rivalry in all of Major League Baseball is set to produce yet another chapter in this storied rivalry. In 2026, the Yankees will once again host the AL Wildcard series against Boston in the Bronx. Boston’s lefty-heavy pitching staff is set up extremely well to take on the Yankees’ lefty-laden lineup. The biggest question facing the series will be whether or not the 2025 AL MVP Aaron Judge will be on the postseason roster after an injury-plagued 2026 campaign. A fully healthy Aaron Judge could have made a mountain of a difference in this series for the Yankees. However, even if Judge were to be on the roster, one would have to believe he’d be doing so at a diminished capacity. It will take other players on the Yankees roster to step up in big ways to try and help mitigate the likely loss of Judge for this series, and potentially the rest of the postseason.

For New York, the emphasis and their most likely path to winning rely on their pitching staff. If the Yankees can get a few timely hits, quality error-free defense, along with their tremendous pitching, then New York has a legitimate chance to move on from the AL Wildcard round just as they did one year ago. However, should the Yankees play sloppy defense, the Red Sox will take full advantage. Don’t expect Boston to simply roll over and play dead just because the games are being played in the Bronx rather than at Fenway. The Red Sox will head into New York looking to silence the crowd early and give themselves their best chance to advance to the next round.

CHICAGO CUBS VS. SAN DIEGO PADRES

This series is arguably the hardest to quantify of the four Wildcard series. San Diego has been one of the best offenses in baseball over the past month-plus. However, the Friars are running into the unquestioned best defensive team in baseball, after the Cubs set the new single-season Statcast Era team Outs Above Average record with +72. One also would need to factor in that this game is being played in San Diego, instead of the extremely weather-volatile ballpark that is Wrigley Field in Chicago. Nevertheless, the teams match up well, and it would behoove the Cubs to strike early against the quality starters of the Padres. Because if this were to become a bullpen game, as most postseason games become, that advantage becomes decidedly in the favor of San Diego. The Padres have arguably the best bullpen in baseball and arguably the most feared closer in the game today, “The Reaper” Mason Miller. And for as good as Miller has been all season, in September, he wasn’t even the Padres best reliever. Chicago will need to try and capitalize early if they want the hopes of advancing to the next round of the postseason.