Most intriguing post-season matchups for the Blue Jays if the playoffs started today

Matchup #3: Boston Red Sox (68-56) currently in the first Wild Card spot

Another division rival for the Blue Jays and a team the Blue Jays have played very well against in 2025. Toronto is 7-3 against Boston, but they haven't met since a three game set at Fenway Park from June 27-29, when Toronto took two of three.

Aside from the division rival angle, there would be interest in the fact that the Blue Jays and the Red Sox have been two of the hottest teams in MLB for most of the summer. Boston is 39-24 since the beginning of June while Toronto is 43-23 over that same stretch.

As well, the Blue Jays were heavily rumored to have interest in third baseman Alex Bregman, who signed with Boston in the offseason. Meantime, Guerrero Jr. crushes the ball at Fenway, hitting .348/.424/.594 with an OPS of 1.018 in 53 career games there, with 72 hits and 11 home runs and 18 doubles in in 207 at-bats.

The pitching matchups would also be a lot of fun in this series with Garrett Corchet, Brayan Bello, Lucas Giolito and Walker Buehler on one side and Scherzer, Shane Bieber, Kevin Gausman and José Berrios on the other.

Honorable mention: Cleveland Guardians (63-58) 1.5 games out of final Wild Card spot

If the playoffs did start today, the Guardians would have missed the post-season, but the fact that they are so close, and playing good baseball lately, we shouldn't count them out just yet as they would be a highly anticipated matchup for Toronto. These two teams faced off in the 2016 ALCS, with Cleveland coming out on top, so you once again have a rematch in the waiting - albeit ten years later.

You also have two teams that have frequently made player transactions with each other over the last few years, including almost a handful within the last 12 months. It started with the Blue Jays acquiring Andrés Giménez and Nick Sandlin in the offseason for Spencer Horwitz (who now plays with Pittsburgh). It continued with the Blue Jays picking up Myles Straw in what was perceived to be a lateral move to make room for Roki Sasaki, but it didn't work out that way. However, that may have been for the best for the 2025 Blue Jays, as Straw has done his fair share of contributing this season.

Finally, at the deadline, the Blue Jays made a one-for-one deal sending a highly regarded pitching prospect in Khal Stephens in return for an injured, but recovering former Cy Young award winner in Bieber.

The Blue Jays and the Guardians have also played some exciting games this season, splitting the season series 3-3 with Toronto ahead 32-24 in the overall runs scored category. Clevelan also boasts some really fun players to watch in José Ramirez, Steven Kwan, Carlos Santana, Canadians Bo Naylor and Cade Smith and electric closer Emmanuel Clase. The Guardians also went all the way to the ALCS last season, so they have a ton of players who have deep post-season experience.

Not to mention the fact that the Blue Jays President, Mark Shapiro, and General Manager, Ross Atkins, were long time employees of the Guardians organization, and there may be a little extra motivation to win a series against this group.