After years in the tag team division, Jeff stepped up and took on The Undertaker in a Ladder match for the Undisputed Championship. Jeff came up short, but earned the Undertaker's respect. Jeff competed for singles titles on several occasions, but was unsuccessful. Finally, the Hardy Boyz split apart, as Jeff continued to pursue his singles ambitions and brother Matt was drafted to SmackDown! and Jeff continued on RAW. After this he would tease a heel turn by attacking several superstars.
Jeff was in few angles after that. He first teamed with Shawn Michaels and then hooked up with Trish Stratus after saving her from Steven Richards and Victoria. In his last match before being released, Jeff was defeated by The Rock. Jeff was released from WWE on April 22, 2003. The reasons given for the release were Jeff's erratic behavior, frequent drug use, refusal to go to rehab, deteriorating ring performance, as well as constant tardiness and no-showing events.