There’s not much World Series experience to speak of when it comes to this year’s Fall Classic. Across both the Tampa Bay Rays and Milwaukee Brewers, there are only three total players who’ve played in the World Series before. In this year’s matchup, two of those players belong to the Rays, and one belongs to the Brewers.
This will be one of the most fascinating World Series in MLB history, as neither team has won a championship before. The Rays have appeared in the Fall Classic twice since becoming a franchise in 1988, falling to the Philadelphia Phillies in 2008 (4-1) and the Los Angeles Dodgers in 2020 (4-2).
As for the Brewers, they’ve appeared in the World Series only once since becoming a franchise in 1969, losing to the St. Louis Cardinals in seven games when Milwaukee was a part of the American League.
We will be guaranteed a first-time champion, making it a must-see World Series. These two teams are evenly matched and will have to count on what got them here. They can’t count on much past World Series experience like teams before them. As we get into this series starting Friday, let’s take a look at which three players have played in the Fall Classic before.
Players Appearing In 2026 Fall Classic With Previous World Series Experience
Steven Matz
Current team: Tampa Bay Rays
World Series team: New York Mets (2015)
The last time Steven Matz made a World Series, he was a rookie starting pitcher for the Mets in 2015. He had only started in six regular season games before getting called upon in the postseason. In those six starts, Matz went 4-0 with a 2.27 ERA. He then started a game in both the NLDS and NLCS, giving up three earned runs and one earned run a piece.
Matz got the call in Game 4 of the 2015 World Series against the Kansas City Royals, going five innings and giving up two earned runs with five strikeouts, earning a no decision. The Mets led the game 3-2 when Matz departed but couldn’t hold onto the lead, eventually losing the game 5-3 and the series 4-1. This was his first and only appearance in the Fall Classic.
Now he comes into the 2026 World Series as a reliever for the Rays. Up to this point, Matz has only made one postseason appearance in 2026, and that was in Game 3 against the Cleveland Guardians in the ALCS. He was excellent in that relief appearance, going two innings and giving up no runs, no hits, and striking out two. The Guardians ended up winning the game to go up 2-1 in the series, but the Rays stormed back with three straight wins to take the series.
Albeit in one game in 2015, Matz is the only pitcher for the Rays in the 2026 World Series to have experience on the big stage.
Dustin May
Current team: Milwaukee Brewers
World Series team: Los Angeles Dodgers (2020)
Not only is Dustin May the only current Brewer to appear in a past World Series, but he’s the only player on either side that has won a championship. He did so with the Dodgers in 2020 (whether you think it deserves an asterisk or not). He is now facing the same team he once beat in the 2020 Fall Classic, the Rays.
He had two appearances in that World Series, both in relief. May came into the fourth inning of Game 2 against the Rays with his team down 1-0. Over the course of an inning and a third, he gave up three earned runs on three hits, with two runs coming via a home-run shot. That was pretty much the difference, as the Rays won the game 6-4.
May bounced back in a big way in his next relief appearance. He relieved Clayton Kershaw in the sixth inning of Game 5 and took control from there. May pitched an inning and two-thirds, giving up only one hit and no runs while striking out a pair. The Dodgers were up 4-2 when May entered the game, and that ended up being the final score, helping facilitate a perfect bullpen outing.
His final numbers in the 2020 World Series through two appearances were three innings, five hits, three earned runs and three strikeouts.
The veteran pitcher has had his ups and downs so far this postseason, but with May being the only player on the Brewers roster who has World Series experience, he could be leaned on and off the field.
Yandy Diaz
Current team: Tampa Bay Rays
World Series team: Tampa Bay Rays (2020)
Like May, Yandy Diaz also played in the 2020 Fall Classic, but for the opposition, although he didn’t get to go head-to-head with May. That was Diaz’ first World Series and he hasn’t been back since, until this season. He’s still with the Rays, whom he’s been with since 2017.
Given that he’s a fielder and a designated hitter, Diaz has the most experience of any player heading into the 2026 World Series in terms of games played with five.
Diaz didn’t particularly have great overall postseason numbers in 2020, hitting .194 with seven hits in 47 plate appearances, scoring three runs, and had an RBI. That RBI came in the World Series when he hit a triple in Game 5 to put the Rays on the board, making it only a 3-1 deficit. He then came around to score on a single to make it just a 3-2 game, but it wasn’t enough, as the Dodgers won the game 4-2 and eventually the series, as mentioned.
His overall numbers in the 2020 World Series: .333 batting average, four hits, one RBI, and one triple in 12 at-bats. It’s worth noting that Diaz missed the last 24 games of the regular season due to a strained right hamstring and was dealing with the lingering effects heading into the postseason, pointing to some of his struggles.
In 2026, Diaz hit 22 home runs with 85 RBI in the regular season and, leading into the World Series, hit .308 with four doubles, seven runs, two home runs and four RBI in nine postseason games. Diaz comes into this World Series healthy this time around and might be the most complete hitter on either team. Who knows, maybe he will have a chance to face May this time around.
Main Image: David Richard-Imagn Images
