1999 Harley became pregnant with Phillip's baby. She gave birth to Zach. Phillip and Beth were stranded on a mountain after a helicopter crash. While making a goodbye video for Lizzie they made love on camera. They were rescued and went on with their separate lives.

2000 Beth discovered she was pregnant with Phillip's child. Phillip reluctantly agreed to keep the child's paternity a secret. Edmund discovered the video of Phillip and Beth on the mountain. Lizzie was diagnosed with leukemia and only a bone marrow transplant from Beth's child could save her. Phillip confessed the truth about the baby to everyone. Beth's son, James, was born, saving Lizzie's life. Harley and Phillip divorced.

2001 Phillip learned that Harley was pregnant, but the child was Rick's. Phillip was worried about Beth's relationship with Edmund. Edmund locked Beth away and she apparently died.Phillip was shocked to see Beth in Springfield, her memory gone and behaving very strangely.

2002 Beth turned out to have an alternate personality, "Lorelei." Phillip and Beth were trapped in a mine. Beth freed them from the mine and they reunited. Phillip fell for Alan's fiancee Olivia. Phillip observed a confused Beth kissing Billy. Olivia and Phillip made love. Beth and Phillip agreed to separate. Phillip and Olivia forced themselves to stay apart and Olivia married Alan. Alan discovered that Olivia and Phillip had kissed before his wedding and threw her out of the house. Olivia and Phillip finally got together.

2003 Alan schemed to keep Olivia and Phillip apart. Olivia discovered she was pregnant and Phillip agreed to support her. Lizzie threatened Olivia and tried to kill herself. Phillip asked Olivia to marry him to give their child a home. Due to Lizzie's threats, Olivia left town without answering Phillip's proposal. Phillip's guilt over Lizzie's mental state and Olivia's absence made him paranoid and delusional. Phillip checked himself into Ravenwood Mental Hospital. Olivia returned and told Phillip that their baby had died, worsening Phillip's state.

2004 When Phillip started to improve, he and Olivia were married. Olivia revealed that their baby, Emma, was alive after all and brought her to the hospital.Angry at Olivia's deception, Phillip plotted revenge.