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This is, of course, a matter of opinion. There is no way to objectively determine who “won” these confrontations. On the whole, I would argue that no one won these confrontations. However, the West clearly won the Cold War as a whole.
One could argue that the US won the Korean War. However, I do not think either side really won. You could say that the US won because it repelled the North Korean invasion and restored the sovereignty of the anti-communist South Korean state. However, it is hard to say that the US truly won when its forces were driven out of North Korea when the Chinese entered the war. The war ended in something of a stalemate and it (arguably) helped embolden China and the Soviet Union because they were able to fight fairly successfully against the US.
One could say that the communists won in Cuba. However, I would argue that it was not much of a victory. We can argue that the communists won in Cuba because they took a non-communist country and made it communist. It remains communist to this day. However, Cuba did not do much to help the Soviet cause as a whole. Cuba led to humiliation for the Soviets in the Cuban Missile Crisis. It also needed to be propped up economically by the Soviets. Communism in Cuba did not lead to widespread communism in Latin America more generally. Therefore, I see little tangible gain for the Soviets.
Overall, I would argue that neither side won these confrontations. Neither side got any decisive advantage in either instance.
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