Checkers dream meaning is explained below using 6 different sources. Each interpretation is shown with its source.

Interpretation 1 — Martha Clarke

Black and white combo boxes symbolize the confrontation of forces in the life’s battlefield. Therefore, depending on how you play checkers that is the way you will behave in real life. Usually, this struggle of antagonisms announces that there will not be great changes in your personal affairs. Winning the game, however, is always a good sign because it suggests the successful end of a risky operation. 
Source: The Big Dictionary of Dreams Author: Martha Clarke

Interpretation 2 — Dream Explanations - Anonymous

Dreams of checkers symbolize competition, strategy and that you are playing a game and attempting to anticipate your opponent’s next move. You are feeling challenged and are attempting to make a winning move in your life.

See Competition and Game.

Source: Strangest Dream Explanations Author: Dream Explanations - Anonymous

Interpretation 3 — Gustavus Hindman Miller

To dream of playing checkers, you will be involved in difficulties of a serious character, and strange people will come into your life, working you harm.

To dream that you win the game, you will succeed in some doubtful enterprise.

Source: Ten Thousand Dream Interpretation Author: Gustavus Hindman Miller

Interpretation 4 — Stearn Robinson - Tom Corbett

Win, lose, or draw, a dream featuring a game of checkers promises a happy future whether you played or just kibitzed.
Source: The Complete Guide to Interpreting Your Dreams Author: Stearn Robinson - Tom Corbett

Interpretation 5 — Raymond Buckland

Playing checkers indicates you will be involved in an argument with others.

See also Chess.

Source: Gypsy Dream Dictionary Author: Raymond Buckland

Interpretation 6 — Ella Freeman Sharpe

See Games.
Source: Psycho Dream Interpretation Author: Ella Freeman Sharpe