In a one word answer: no, . . . experience does not trump training.
Apparently, experience can and often does trump training. Cops get beat with some regularity by untrained but experienced bad guys.
Go from Viet Nam up to the present: in every conflict the USA has been outnumbered in terms of soldier vs soldier numbers, . . . and yet the body count total has always been in our favor, in many cases by 10+ to 1.
In Iraq and Afghanny, . . . I have been led to believe that the numbers are even further apart, . . . and the only thing that makes the difference is that our men have the training, . . . rugheads have weapons, indoctrination, and desire. An M-4, . . . an M14, . . . or a Barrett, . . . trumps desire and indoctrination every time.
The only difference is not that our guys have the training, LOL. It certainly helps, but in each of the conflicts you listd, we have had tremendous superiority in technology, munitions, transportation, and medical care. In the recent engagements, our guys have also had the benefit of wearing very good ballistic armor. We have the ability to strike our opposition from altitudes they can't reach or from locations hundreds or even thousands of miles distant. Injured soldiers can be evacuated extremely quickly from many areas of combat, usually after receiving first aid on the ground, then getting further aid back at base and/or then transported to a hospital. After being stabilized, soldiers can be in Germany or back in the US for additional treatments within a couple of days of being injured.
American soldiers may be better trained than their opposition and that does help, but American soldiers also have many other very significant advantages. If a group gets pinned down, they can call in for and often get air support or artillary support.
Even when not on their home soil, the American military often has numerous advantages over its opposition