It is amazing how many matches come right down to the wire. I believe it has something to do with the fact that the leader in a match must be conservative with the cube and his plays, and the player who is behind tends to be more aggressive with his cube and plays. This often causes matches to become very close at the end of the match. And just like the last two minutes of a football game, or the last inning of a baseball game, this is often what separates the winners from the losers.
There are some very definite strategies to employ, as a general rule, toward the end of a close match. Let's look at some of the possibilities.
If both players are 2-away from winning (let's say the score is 5 to 5 in a match to 7), the cube strategy is very simple, but often misunderstood and misplayed. At this point in the match, both players have a 50/50 chance of winning at the start of the game. Very shortly, however, one player is bound to have an advantage, even after only one or two rolls. As soon as that happens, the player with the advantage should double. Even if he is only a 1 percent favorite to win, he should double. It's that simple. If you are favored, you would rather play this game for the entire match than just play it for one point. If you don't double, you risk getting to a position where you become so good that when you do double, your opponent should drop, and you only win 1 point instead of the match.
Now, if you are doubled at this score, you should take if your odds of winning the game are better than 31 percent. The reason that your take-point is 31 percent is that, if you drop and the score becomes 5-6 Crawford in a match to 7, you must either win 2 games in a row or win a gammon on the first game in order to win the match. And the odds of doing that are 31 percent. (Crawford means you cannot double for one game after your opponent reaches 1-away form match.)
Another typical close-game score is when your opponent is 2-away from winning the match, and you are 3 or 4 away. At this score, it is a common mistake to simply give the cube right away regardless of the checker position. By doing this, you give your opponent a chance to win the match without doubling and without having to win a gammon. So you should only double when you are clearly ahead. However, if the situation is such that there is a high risk of gammons for your opponent, even if you are only a slight favorite in terms of wins, you should double. The reason is that once you double, gammons give you 4 points, which is very valuable and might even win you the match. But gammons are of no benefit to your opponent, who only needs two points. So after you double at this score, you get the benefit of both winning single games and gammons, but your opponent only benefits from single games.
In the above situation, if you are the player who is leading, and you are 2-away, you should not be doubling unless you have such an extremely strong position that your opponent must either be forced to drop or he has to take a cube where he has very little chance to win. At this score, your strategy is to win without the cube, either by winning two games in a row, or by winning a gammon with the cube in the center.
And the third very common situation is when you are both 1-away from winning, or when the cube has been turned so that whoever wins the game wins the match. This is called Double Match Point, or DMP. At DMP gammons and backgammons have no meaning to either side, so it is important to make all of your checker plays with that in mind. If gammons don't matter, you should be more interested in just winning the race if you are ahead, and not worry about trapping your opponent or trying to pick up more checkers to win gammons. Your bearoff plays should be with safety first in mind, and not getting the most checkers off to win gammons. Conversely, since you don't have to worry about getting gammoned, if you are behind in the race, don't be afraid to get into massive back games and blocking games. If these are well-timed, they win a lot of games. Normally, you avoid these games because if they go wrong, you get gammoned a lot.
The key to close-match strategies is to carefully think through the options: how does the score affect your checker and cube play; how important is a gammon for me or for my opponent; what can I do to maximize my advantage or minimize my opponent's advantage. How you make these decisions truly separates the winners from the losers.