While on "Oz", Winters did guest shots on network series like "Millennium" and "New York Undercover" (both Fox), playing on the latter series a firefighter suspected of setting blazes who happens to be the brother of one of the resident detectives (Marisa Ryan). Here Winters teamed up with "Oz" co-star Lauren Velez for one 1998 episode, but he would reteam with "Oz" co-star Christopher Meloni for a series, both actors taking roles on the other side of the law, co-starring as detectives on the NBC spin-off "Law & Order: Special Victims Unit" (1999-2000). On this drama, he was cast as Brian Cassidy, an enthusiastic and relatively green detective assigned to this elite unit who gets paired up with veteran Detective Munch (Richard Belzer), late of the Baltimore Police and a character from the acclaimed series "Homicide: Life on the Street". Viewers of "Oz" were interested to see Winters tackle such a different role, playing the idealistic and eager-to-please lawman on this police drama. His character's inability to handle the emotionally harrowing terrain of the Special Victims Unit excused the actor from the series midway into the first season, when he returned to lens the fourth season of "Oz".

Winters' feature work includes a small role in the Julia Roberts and Mel Gibson thriller "Conspiracy Theory" (1997). He subsequently starred as a dissatisfied writer left to care for a little girl who turns out to be his daughter and inspires him to a more fulfilling life in the family drama "Undercover Angel" (filmed in 1998), was released direct-to-video in 2000.