When playing a RTS (skirmish - single player) usually there is a moment after which the player holds most of the map, most of the resources and his units compared to the AI are 7:1 or something like that. In this situation the possibility to loose is very small, almost impossible. But the enemy still has power and the player must destroy it playing 10, 20 or more minutes.
Scenarios:
1. Win when you hold 70 or more % of the resources (or territory) - as in Rise of nations. That is not valid for the AI, because the player could survive with only one base... maybe.
2. Let the player smash the enemy, the situation will become more and more hopeless for the AI. Maybe that will be fun or maybe not?
3. The enemy will have hidden feature when is in bad situation to pull out very special power/unit so it can crash your army and then the gameplay will become more dynamic because it will take a lot of territory and a lot of players unit will be destroyed, the player can even lose. But what the next time - the player will get the territory around the enemy base again, should this happen again? And maybe the same for the player - when he is in bad situation holding only his base to receive bonus?
In the chess at the end of the game, endschpill (?) figures are less and usually most units are destroyed, so even the King could do something. But in RTS usually the winning side will have a lot of powerful and upgraded units. And not even at the end, usually there is a point after which A will become stronger than B and that can not be changed easy.