This guide is a comprehensive look at the Boston Red Sox's 2025-2026 offseason schedule, including essential dates on the Winter Meetings, MLB Draft Lottery, and dates on which the Red Sox have to make important decisions on their arbitration-eligible players and players with a team or mutual contract options. In the following paragraphs, you will find a list of pending free agents, players with contract options, and a detailed timeline of the MLB offseason.

The Red Sox overhauled the backend of their roster and made depth moves with the Rule 5 Draft in mind. Craig Breslow managed to protect those he wanted while flipping others for depth pieces and younger prospects.

The hot stove is now fully aglow. Here are our panel's top 50 free agents for the 2025-26 MLB offseason, along with our best guesses at the contracts they'll receive.

The hot stove is now fully aglow. Here are our panel's top 50 free agents for the 2025-26 MLB offseason, along with our best guesses at the contracts they'll receive.

The Red Sox offseason rumor mill is heating up!

Detroit Tigers' ace Tarik Skubal is rumored to be on the trade block this offseason. What would a potential trade package look like for the Red Sox to acquire him?

The Red Sox overhauled the backend of their roster and made depth moves with the Rule 5 Draft in mind. Craig Breslow managed to protect those he wanted while flipping others for depth pieces and younger prospects.

Chris Cotillo of MassLive reports that the Boston Red Sox are likely to tender a contract to starting pitcher Tanner Houck.

The Red Sox have until November 18 to protect prospects from the Rule 5 Draft by adding them to the 40-man roster. Fortunately, most prospects they would want to protect are already on it, but what about the few who aren't?

The Royals need outfield help, and Kris Bubic could be a good fit with these four teams.

The Royals need outfield help, and Kris Bubic could be a good fit with these four teams.

The Red Sox have plenty of talent roaming the outfield. There is no reason to delay the inevitable any further.

New to the DiamondCentric stable of sites is this searchable, sortable list of available free agents.

New to the DiamondCentric stable of sites is this searchable, sortable list of available free agents.

A spike in FIP, wOBA, and xwOBA in 2025 complicates the left-hander’s bid for a long-term deal.

A spike in FIP, wOBA, and xwOBA in 2025 complicates the left-hander’s bid for a long-term deal.

Kristian Campbell is abandoning second base for the outfield. It's tough to figure out why this is the best decision for both him and the team.

Tatsuya Imai is likely to be the crown jewel of the 2026 crop of NPB stars making their way to America. Who is he as a pitcher, and what might make him a special player in Major League Baseball?

After a dominant 2024 campaign and an injury-shortened 2025 season, former Padres and Yankees pitcher Michael King enters free agency as one of baseball’s biggest wild cards.

Who will sign one of the most controversial, premier free agents in baseball?

A former Red Sox outfielder has found a new home.

Rumors are swirling as the Red Sox expect to have a busy winter.

Rumors are swirling as the Red Sox expect to have a busy winter.

Drafted in 2022, Dalton Rogers has spent time sharpening his arsenal after dominating with only his fastball in college. The 2025 campaign was a tantalizing proof of concept, as he struck out 129 batters in 105 innings between Greenville and Portland.

Here are three free agent starter the Red Sox should consider this winter.