This is quite a good video from Sifu David Ross of New York Sanda that talks about the history of challenge matches in the Chinese martial arts, and includes some clips of what has been recorded, plus some great historical photos.
He covers the 1954 Tai Chi vs White Crane challenge match in Macau, the Hong Kong rooftop challenges in the 1950s, and the Kung Fu vs Muay Thai matches that began in the 1920s.
As you’ll see, the fantasy of the “Kung Fu Master” doesn’t always match the reality. The one thing it does show is that it doesn’t matter how good you are at forms, iron body demonstrations, push hands and compliant applications, if you want to be able to use your art, you need to spar against resistance. That’s something to never forget.
Here the 1954 Wu vs Chan full fight:
1950/60s roof top fights in Hong Kong: