While the second year of the Overwatch League has yet to conclude, Blizzard has already announced some key dates for the rest of the year, revolving around roster construction and player contracts.
On September 30 the signing window opens for teams to sign players, negotiate extensions, and talk about contracts, while on October 7 teams that have completed exercising or declining existing contract options can submit free-agent player contracts to the League for approval, as well as player trades for approval too.
On November 11 season agreements for 2019 officially expire, with any players not under contract into next season becoming free agents, although they're allowed to talk contracts with other teams before this date. November 15 then marks the deadline for all teams to have a minimum of eight players under contract, although they can sign or trade players until June 15 next year at 17:00 PT.
Players born on or before June 15, 2002 can sign contracts for next season as well, and Contenders and Academy guidelines are unchanged from the last season, although in 2020 Contenders teams associated with an Overwatch League side must compete in the same region as their parent team to be eligible as an Academy Team.
If the Overwatch League team in question wants to operate a Contenders side in a different geographic region though, they must have meaningful local infrastructure in place, and accept that they won't receive Academy team benefits.
Contenders teams associated with organisations may negotiate 'right to match' clauses too, granting the parent team the right to match any offer from a competing OWL side looking to sign a Contenders player. This is limited to seven days from the initial contract submission to the League Office, and if they choose not to match, they may be entitled to receive a buyout fee from the competing team.
Two-way player contracts are also changing as well, as part of feedback from the 2019 season, with a maximum of four players designated as two-way at any given time, subject to the following rules:
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