Series to watch as season hits Memorial Day mile marker

Memorial Day is a key mile marker for the regular season, the point at which we should theoretically have enough information to evaluate all 30 teams.

Theoretically.

In reality, it still feels like anything could happen under the right circumstances in 2026, and we're going to need more data. Lucky for us, quite a few teams we still have lingering questions about will be facing off against each other in the week ahead. Check back on June 1, we're sure we'll have those evaluations ready by then.

Here are five series to watch for the week of May 25.

Cubs at Pirates
3 games (Monday-Wednesday)

Head-to-head: The Cubs went 10-3 against the Pirates last year -- outscoring them 54-26 -- and then got something of a rude awakening when they got their first look at a much-improved division rival back in April. They lost that first series of 2026, two games to one, and needed a comeback (and a walk-off) in the finale to salvage anything at all.

Storyline: Something has to give here. The Cubs, who have already had two 10-game winning streaks this season, come into the series having lost eight in a row and 12 of their last 14. The Pirates, meanwhile, have spent the month climbing a few games over .500 before immediately erasing all that progress and starting over again. Every game has a winner and a loser, so it stands to reason that this could be a jumping-off point for one of these teams -- both rosters are far too talented to carry on like this.

Watch out for: Konnor Griffin may not be the only up-and-coming Pirate settling in. Spencer Horwitz remained a bright spot for the scuffling Bucs with a leadoff home run against Dylan Cease on Sunday and is now hitting .306/.405/.516 (.921 OPS) in May.

Cardinals at Brewers
3 games (Monday-Wednesday)

Head-to-head: The Brewers and Cardinals split their first meeting earlier in the year, winning a game each around a rainout. The Brewers just took the 2025 season series, 7-6.

Storyline: Look, if we're to keep up with the NL Central, we're going to have to adopt "toddler with a permanent marker" protocol -- we cannot take our eyes off of it. So it's Brewers-Cardinals up top now, although to be clear, only 4 1/2 games separate the first-place Brewers (30-20) and the last-place Pirates (27-26), which is why week-to-week things can look so different. It's a three-game series, and the Cardinals are in second place, a game and a half back, so it's not like too much ground can be lost or made up in this series, but the Brewers have objectively played better baseball, so this should be something of a test of the Cardinals' readiness to contend in this division.

Watch out for: Strong evidence that the winner of the Rafael Devers deal was, in fact, the Milwaukee Brewers. In the short term, at least. Kyle Harrison, acquired by the Red Sox from the Giants last June, was bundled into a lower-profile trade to the Brewers just before Spring Training. Turns out that was a great move for the Brewers, who have gotten more out of Harrison (nine starts, 1.77 ERA, 11.6 K/9) than they have any pitcher, non-Jacob Misiorowski division. Harrison is scheduled to start on Wednesday against his closest counterpart on the Cardinals, 25-year-old Michael McGreevy, who's pitched to a 2.40 ERA with a 0.99 WHIP in his ten starts.

Twins at White Sox
4 games (Monday-Thursday)

Head-to-head: After really beating up that extremely unfortunate 2024 White Sox team (12-1), the Twins actually lost their 2025 season series (5-8). This will be their first meeting of 2026

Storyline: Hey, so the White Sox aren't half bad. Entering Monday, they're a .500 team -- which, admittedly, doesn't sound good, but it's good enough for second place in the AL Central, and this team is coming off three consecutive 100-loss seasons, so let's be fair. The Twins, who were also pretty terrible in 2025, are only a half-game behind them, at 26-27 after sweeping the Red Sox in Boston over the weekend. Two potential redemption arcs in progress -- but is one bid stronger than the other? We may have a better idea after this series, because these intradivision matchups are key, and coming into this week, the White Sox have only seen the Royals -- not great competition to this point in the season.

Watch out for: Byron Buxton really is all the way back. (He never really left, but "Byron Buxton remains good" doesn't sound as good.) Point being, in 15 May games, Buxton is now hitting .281 with eight home runs and 15 RBIs. Probably not a complete coincidence, then, that the Twins have now won six of their last seven games.

Yankees at Athletics
3 games (Friday-Sunday)

Head-to-head: The A's won the first head-to-head series in 2026 back in April at Yankee Stadium, two games to one, and now this new-look team needs just one win at home to buck a nuisance of a recent trend -- they last won or split a season series against the Yankees all the way back in 2019.

Storyline: File both under "clubs we need to see more from." As of Monday, the A's are in first place in the AL West but just one game above .500 (27-26), stacking up offensively while their pitching leaves a lot to be desired across the board. We can't reasonably come down that hard on a team with a .585 winning percentage, but the Yankees can't coast on their reputation (i.e. their March/April record) for much longer, either. They're now 5-10 and averaging three runs per game since their May 8-10 series against the Brewers, a disaster their bullpen was not built to weather. Both of these teams could be first-place finishers and postseason favorites … just not like this.

Watch out for: Sophomore slump? That's adorable. Nick Kurtz is only getting hotter, even if the home run stroke isn't quite back yet. Through Sunday, Kurtz is now hitting .350/.480/.563 (1.043 OPS) with 22 RBIs this month.

Phillies at Dodgers
3 games (Friday-Sunday)

Head-to-head: The clubs will be meeting for the first time since the 2025 NLDS, which the Dodgers won in four, but in the regular season, the Phillies have been getting their way more often than not, going 9-3 against the Dodgers since 2024.

Storyline: The gut-wrenching end to their 2025 postseason matchup feels like a lifetime ago at this point, thanks in large part to the perfectly ridiculous journey the Phillies have already taken us on in 2026. The Phillies are now 17-8 under onetime Dodgers skipper Don Mattingly, hovering around .500 much sooner than they had any right to given how things started. That said, the past week had proved a bit challenging -- they just had a 2-4 homestand against the Reds and Guardians -- and the week ahead won't be any easier. Worth noting: the Phillies' offense seems to be stalling again, hitting a collective .201 with a .621 OPS since May 11 (29th and 26th in MLB in that time span, respectively), and Dodgers pitchers rank second in baseball this season in both ERA (3.10) and batting average against (.211).

Watch out for: Another week, another Dodgers veteran picking up the slack. Currently it's Teoscar Hernández, who since May 11 is hitting .383 with four doubles, three homers and 14 RBIs in 13 games (including a six-RBI day in Milwaukee on Saturday in which he went 3-for-4 with a home run.)