Accounts of Wong's fight with Lee are controversial, as it was unrecorded and held privately at Chinatown, Oakland in 1964, when both men were in their early 20s. According to Linda Lee Cadwell, Bruce Lee's wife, Lee's teaching of Chinese martial arts to white people made him unpopular with Chinese martial artists in San Francisco. Wong contested the notion that Lee was fighting for the right to teach whites as not all of his students were Chinese. Wong stated that he requested a public fight with Lee after Lee had issued an open challenge during a demonstration at a Chinatown theater in which he claimed to be able to defeat any martial artist in San Francisco. Wong stated it was after a mutual acquaintance delivered a note from Lee inviting him to fight that he showed up at Lee's school to challenge him. According to author Norman Borine, Wong tried to delay the match and asked for restrictions on techniques such as hitting the face, groin kicks, and eye jabs, and that the two fought no holds barred after Lee turned down the request. The details of the fight vary depending on the account. Individuals known to have witnessed the match included Cadwell, James Lee and William Chen, a teacher of T'ai chi ch'uan. According to Linda, the fight lasted three minutes with a decisive victory for Bruce. Lee gave a description, without naming Wong explicitly, in an interview with Black Belt. Cadwell recounted the scene in her book : This is in contrast to Wong and William Chen's account of the fight as they state the fight lasted an unusually long 20–25 minutes. Wong was unsatisfied with Lee's account of the match and published his own version in the Chinese Pacific Weekly, a Chinese language newspaper in San Francisco. The article, which was featured on the front page, included a detailed description of the fight from Wong's perspective and concluded with an invitation to Bruce Lee for a public match if Lee found his version to be unacceptable. Lee never made a public response to the article. Because Lee never responded to this public request, also closed his school, and moved out of the area shortly after the fight, the Chinese martial arts community in San Francisco concluded that Lee lost. An alternative, eye witness, account of the fight is detailed in the book Showdown in Oakland: The Story Behind the Wong Jack Man - Bruce Lee fight, by Rick Wing. This version contradicts the long established mainstream story, attributing the fight to an acceptance of Bruce Lee’s open challenge, rather than an attempt to stop Bruce Lee teaching non-Chinese. In Wing’s book, Bruce Lee strikes unfairly at Wong Jack Man during the pre fight ‘bowing’ stage and - later during the 20 minute fight - is trapped in a headlock by Wong Jack Man, who went through the motions of debilitating Bruce Lee but did not strike as it would have been a dangerous move. Furthermore, Wong Jack Man elected not to use his highly developed kicking skills in the fight, as they would have given him an advantage over Bruce Lee’s 1964 level of kicking abilities. Wong Jack Man stumbled over a low display platform - initiating the end of the fight - at which point Bruce Lee leapt on him in a frenzy, and had to be pulled away by the observers. Though Bruce Lee was shouting for Wong Jack Man to yield, no submission was given. In "Bruce Lee: A Life" by Matthew Polly, who shares a few insights from his extensive research and interview process, he says that according to David Chin, who arranged the match on Wong’s behalf, Bruce overwhelmed Wong with his opening series of attacks, causing Wong to turn his back and run. Bruce chased him around the room until Wong tripped and fell. Bruce jumped on top of Wong and rained down punches, forcing Chin to intervene and rescue Wong. Wong later expressed regret over fighting Lee, attributing it to arrogance, both on the part of Lee and himself.
Wong instructed classes at the Fort Mason Center in San Francisco, and in Oakland, CA, at the First Unitarian Church, for the better part of five decades before retiring in 2005. Wong Jackman's two top students continue his legacy of teaching. In San Francisco, Ca, Rick Wingteaches classes at a private location. In San Rafael, and San Anselmo in Marin County, CA, runs the that teaches Wong Jackman's arts. For more information on Wong Jackman's arts and legacy you can read the "Northern Shaolin Special Report" about the Black Sash graduation ceremony held by Scott Jensen and the 10,000 Victories School. Rick Wing has published a large number of books on the Northern Shaolin forms taught by Wong Jackman that also contain many articles about the San Francisco martial arts community and its leaders, while Scott Jensen has published several instructional video programs, all are available on Amazon. Wong died in California on December 26, 2018.