January
Recruit Replacement GMs - Fill unpaid/orphaned teams
League Survey - Hold votes for rule tweaks or improvements
Confirm League Settings - Lock in any rule changes in advance of the MiLB Draft
February
MiLB Draft - Prospect draft begins
Finalize Team Rosters - Ensure all rosters are legal ahead of Free Agency
March
Free Agency Opens - Begin bidding/signings
Regular Season Begins - Lineups active; scoring starts
Extension Window Opens - Submit player extension requests
April
Regular Season Continues
May
Regular Season Continues
Midseason Activity Check - Contact any inactive GMs
June
Regular Season Continues
Salary Cap Fluctuation Calculated for next season
July
Regular Season Continues
Trade Deadline
August
Regular Season Ends
Playoffs Begin
Free Agency Closes
Cap Transactions Freeze
September
Playoffs Continue
Playoffs End - Champion crowned
Extension Window Closes
October
Payouts Awarded
Market Value Adjustments for next season
Offseason Begins
November
League Season Rollover - New season initialized
Draft Lottery - Determines order for next year's MiLB Draft
Trades & Cap Transactions Reopen - For paid/confirmed GMs only
December
Recruit Replacement GMs - Fill any open teams
Renewal Payments Due - Deadline for returning GMs
Rule Discussions/Proposals - Prep for January vote on changes
