In 1998 Wilson co-wrote and directed his biggest cult hit at the time, Bio Zombie, which was influenced by Dawn of the Dead and takes place in a shopping mall, where a small group of misfits bands together in order to survive.
Yip next directed the 1999 crime-drama Bullets Over Summer, starring Francis Ng and Louis Koo as two detectives hunting a gang of deadly Criminals who have to use a demented elderly woman's (Helena Law Lan) apartment for surveillance. The biggest-budget film of his career up to then, he considers Bullets Over Summer his "turning point". He shared a best-screenplay award at the 2000 Hong Kong Film Critics Society Awards for the film.
In 2000 he was picked by Golden Harvest to direct Skyline Cruisers, a big-budget action film. Yip did not get along with the cast and clashed with the studio's management over creative differences.
Other films include the science-fiction-action story 2002, and the romantic comedies, Dry Wood, Fierce Fire (with Miriam Yeung and Louis Koo) and Leaving Me, Loving You (with Leon Lai and Faye Wong). In 2004, Yip also directed his first wuxia style film, The White Dragon, starring Cecilia Cheung and Francis Ng.
In 2005, Yip directed his most critically acclaimed film, SPL: Sha Po Lang. A gritty return to the 1980s style of Hong Kong action cinema, SPL starred Simon Yam and Donnie Yen as Hong Kong police officers trying to pin a crime on an unstoppable gangster, portrayed by Sammo Hung.
In 2006, Yip re-teamed with Yen for an adaptation of a Hong Kong manga, Dragon Tiger Gate. In 2007 Yip released Flash Point, another martial-arts crime drama in the same vein as SPL. The film starred Donnie Yen, Louis Koo, and Collin Chou.
Yen and Yip's latest collaboration as actor and Director, Ip Man, is a semi-biographical account of Yip Man, the first martial arts master (Chinese: Sifu) to teach the Chinese martial art of Wing Chun openly. It also featured fight choreography by Sammo Hung. The film was released in December 2008 and immediately shot to number one on its opening week in Hong Kong, earning over HK$2.8 million in three weeks.
Ip Man 2, which is produced by Raymond Wong, picks up on Yip Man's life after his migration to Hong Kong where he took on his most famous disciple, Bruce Lee. The film was released 29 April 2010.
In 2014, it was announced that Yip and Yen would reunite for a third Ip Man film, to start filming in early 2015 for release later in the year. The film will be presented in theatres in 3D format for the first time in the franchise.
In 2016, Donnie Yen announced that he and Yip would collaborate once again on a fourth Ip Man film.
