You can change your season settings within your System Settings. It is the last option in the System Defaults tab. Specifically, you'll want to change the "Season Start Month" in order to have the system roll over into a new season.
How do I change the year?You cannot manually change the year. This is automatically calculated based on the start month you select. This is controlling your "Current Season" so your Current Season cannot be a date in the future.
Your Season Start Month will always calculate to a date in the past and will be no more than 11 months in the past. For example, if today's date falls in March 2021 and you set your season start month to April, the system will calculate your season start date to be April 2020, because April 2021 hasn't arrived yet. In the same example, if you set your start month to February, the system will calculate your season start date to be February 2021, because that start date has passed.
Your Season End Month will automatically be calculated by the system by setting your season to be 1 year in length.
Please note: Your season start month is NOT necessarily the month that your games begin. Instead, the season start month is the first month you intend to begin USING the system for the new season. For example, if your games begin in August 2014, but you are going to begin scheduling in June 2014, then your Season start month should be June - NOT August. It can take up to 12 hours for the system to fully recalculate all counters & settings if you make a change to your season start/end months.