They managed to do it fairly often I believe. Certainly more than enough times to chalk it up to luck or coincidence. Again and again, they managed to literally just charge through enemy formations. Sometimes the Hussars managed to break the enemy with their initial charge and rout their opponents before.
http://www.kismeta.com/diGrasse/HowHussarFought.htm
This is a pretty in depth read on how winged Hussars managed to break pike and musket formations. I would take the calculations with a grain of salt but it does provide a good summary.
Long story short, they used a combination of a very dense formation and extremely long lances to plow through a formation supplemented with excellent training and very high morale. The artistic depictions of winged hussars in a charge many times depict them in a running pike wall formation.
What's probably less commented on is the role of artillery and missile fire to help disupt enemy formations so the Hussars could plow through them. Just like Napoleon's use of the column of attack, artillery probably had a pronounced effect on the resulting charge. Support staff always gets the shaft when it comes to history glamor.
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