Of course, it in fact happens all the time. Exactly how often depends on how one cares to define a "military force" - are we talking conventional armies, or irregular forces as well? There are many many examples of insurgency from the 20th century alone
A number of examples can be found just inside Afghanistan, such as the mujaheddin and later Taliban fighting the Soviets and ISAF respectively, in contemporary times; as well as the resistance of the Afghans to the British during the First and Second Anglo-Afghan Wars -although whether the war was won for the afghans during this time is debatable.
In fact the you mentioned quite an excellent example of the Soviets versus the Nazis in World War 2 - although it's quite debatable of whether the Soviets were less well equipped by the time they achieved victory.
The Viet Minh/ Viet Cong guerrillas were vastly overmatched in terms of materiel versus the French and later, the Americans, yet they managed to achieve their strategic objectives - albeit at a terrible cost.
So perhaps another question that might seem silly at first but is worth mentioning is what does "winning" look like in this sense. For example, whilst the U.S achieved its initial objectives of toppling Saddam in 2003, the insurgency did achieve its goals of turfing out the U.S Army and turning the country into a terrorist haven as it stands today, as well as destabilizing the rest of the Middle East.
The North Koreans and Chinese were able to fight the U.N forces in Korea to a stalemate despite being far less well equipped. Whilst their initial goal was unification of the peninsula, that goal changed to "not getting roflstomped by the United States" - so one could argue that in light of how the odds were quite well stacked against them in terms of materiel, they still managed to punch above their weight. Of course, Whited's Law applies.
So any example would require an examination of the actors' desired end-states; that is to say what were their strategic goals and were they accomplished? This might seem easy when looking at the unconditional surrender of the Third Reich from the perspective of the Allies. However, when examining the strategic goals of a poly-actor conflict such as Libya in 2011 the lines become increasingly blurred; the initial states of the rebels overthrowing Gaddaffi were achieved but was the conflict truly "won"? That's harder to argue looking at the state of the country today.
Another example might be Napoleon's invasion of Russia - although Napoleon had the better army and was undefeated militarily he still ultimately lost the war due to the infamous Russian winter.
Ultimately I feel that there are many examples of where forces equipped with inferior equipment have won out but often the reasons are quite complex and just as often have as much to do with the mistakes of the 'better equipped force'. Nazi Germany was arguably better equipped than its antagonists in World War 2 yet repeated strategic blunders cost them the war.
One could argue that in 1940, France had technically the better equipment but its tactical doctrines and strategic calculus were wrong and as a result they were stunningly defeated. Varus and the Roman legions were destroyed in the Teutoberg Forest despite being far better equipped than their adversaries as a result of Varus' incompetence.
So the answer is yes, but often rarely ceteris paribus.