Lily Winters married the Australian Cane Ashby in 2009. He was 12 years older than Lily. Lily became a model for Jabot Cosmetics, and Cane was a bartender at her father's club Indigo. After one miscarriage, Lily was diagnosed with ovarian cancer and had a hysterectomy. But luckily she had the foresight to harvest some of her eggs. Lily's best friend Mackenzie volunteered to be surrogate and soon became pregnant with twins Matilda and Charlie, who were born two months premature. Lily asked Mackenzie to be godmother to the twins, and Lily's adopted brother Devon became their godfather. Cane and Lily broke up numerous times, divorced and remarried, mostly due to Cane's screw-ups and the lies he told to cover them up, usually aided by his father Colin, and some infidelity on both sides. Except for the time that Colin kidnapped the twins and Cane faked his death, they still managed to keep a family atmosphere for the twins to grow up in.

One year when Lily and Cane were split up, the annual Delia Halloween costume party benefit was held at Top of the Tower. A fire broke out on the floors just below, cutting them off from the floor where her children were having their own party. They were rescued from the roof by helicopter and Lily was reunited with the twins who had been led out the front door.

Cane agreed to come home for Christmas eve and morning with the twins, staying in the guest room. Neil and the kids planted some mistletoe, then got the Ashbys to kiss underneath it. Months later, they reconciled.

In late 2016, Neil was playing basketball with young boy grandson Charlie, but by May 2017, Charlie and Mattie had morphed into teenagers and were sophomores attending Walnut Grove Academy. Charlie was popular and confident, and Mattie was smart, shy, and spectacled. Charlie got a summer job as a lifeguard at the Genoa City Athletic Club rooftop pool. Charlie was very charming to the Athletic Club guests, especially one pretty bikini-clad woman named Juliet.

Earlier that year, Cane had gone to Japan where he and a coworker named Juliet had gotten drunk, and he'd gotten her pregnant; both were subsequently fired. Juliet filed a sexual harassment lawsuit against Cane, so the twins had to be told about their impending half-sibling. They were shocked and appalled. When Charlie realized who his favorite customer Juliet was, he told her that if she were drowning, he would pull her out because it was his job, but he wanted nothing to do with her or her kid. After Lily discovered that Cane had used most of the twins' tuition money to pay off a blackmailer, Lily threw Cane out. Feeling guilty and hoping to win Lily back, Cane sold his car and paid the Walnut Grove tuition for the twins.

Meanwhile, young singer/musician Reed Helstrom was dating a fan named Zoey. Reed caught her kissing Charlie Ashby, so Reed and Zoey split up. Reed then became intrigued with Mattie. They began hanging out together when she could, and she would go to see him perform at the Underground. Finding out that her twin brother was Charlie, the guy who had broken up Reed and Zoey, and that Reed was the son of Victoria, who had fired his father, caused the two young men to bicker every time they met. However, once Mattie and Charlie discovered the truth behind Cane's firing, Charlie and Reed called a truce. But when her parents found out, Mattie was forbidden to see Reed. They began meeting on the sly, had their first kiss, with Charlie often covering for her absence. Cane caught them, but after Lily decided to divorce Cane she and Victoria removed the restriction. The twins were devastated by the divorce news, but understood. Charlie was disappointed further when he was not chosen for the football team. But when her parents found out, Mattie was forbidden to see Reed. They began meeting on the sly, had their first kiss, with Charlie often covering for her absence. Cane caught them, but after Lily decided to divorce Cane she and Victoria removed the restriction. The twins were devastated by the divorce news, but understood.

On Halloween, Reed borrowed the key to The Underground from Noah and he, Mattie and Charlie brought their friends intending to have a party. But when they heard Nick arrive they sent their friends home and hid in the store room. Not long after Nick left they realized the place was on fire and they were trapped. Mattie called 911 while Reed called Billy for help, and Charlie left a voicemail for Cane. Billy got inside and rescued them, they got out, but when the building collapsed, Billy’s leg was pinned. Jack arrived, and emotionally insisted on going in. He talked to Billy about forgiveness, and they walked out together with Jack smiling and Billy limping. Lily was reminded why she shouldn’t have allowed Mattie and Reed to see each other again, and Mattie was grounded.

Juliet went into labor, her baby was born via c-section, but Juliet died in childbirth. Cane and Lily named the baby Sam in honor of Cane’s deceased sister Samantha. Sam had a serious heart problem, his medication no longer working, he required cardiothoracic surgery.

After Cane surprised Lily in Paris where she had gone on a business trip, they reunited and Cane moved back home with Sam. Charlie accepted it readily, but Mattie was hesitant to forgive him, and Lily had a hard time dealing with Sam being there, but both gave it their all for the sake of the innocent baby. Both Mattie and Charlie went to work as interns at Hamilton-Winters. Charlie worked for Devon in the music division.

Working for Abby Newman, Charlie edited the video she was making of memories the Abbott matriarch, Dina, before they faded away from Alzheimer's. When finished, Abby and Ashley prescreened and approved it. A theater was rented, the Abbotts arrived in a limo in formal dress. Victor showed up uninvited, but Dina let him stay. Everyone was enjoying the video titled, “What the mind can’t remember, the heart never forgets.” Suddenly a clip where Dina admitted that Jack was not John’s son appeared. Ashley and Abby were shocked, as they had not included that clip to protect Jack. Jack was devastated. Charlie assured everyone that he knew nothing about the clip, and Abby assured him they knew he was innocent. Ashley later revealed that Jack was really John Abbott’s son, how she had coached Dina, edited the clip in the movie of Dina’s memoirs, and had paid the head of the lab to alter the DNA test results.

Shauna, the girl being mentored by Hilary, ran away from her aunt’s where she had been living since her family moved to California to concentrate on her brother’s addiction. Unable to get Hilary’s attention for help, she began hiding out in Charlie’s room. When Cane and Lily found out they offered to let Shawna stay and room with Mattie, who was fine with it. Hilary, who was pregnant with Devon’s child, had just moved into Devon’s guest room, insisted Shawna share the room. Although it was awkward at first, it wasn’t long before Devon asked Hilary to move into his room.

Hilary allowed Charlie and Shauna to use their place to have sex, Lily found out, stopped them, and Shawna ran away. Hilary called Lily a prude. Lily drove as Charlie and Hilary looked for Shawna, while Lily and Hilary argued. Lily ran a red light, and was hit broadside by another car. Lily and Hilary were taken away by ambulance. Lily had no serious injuries, but Hilary was in critical condition and the baby didn’t make it. Devon proposed, gave Hilary a fabulous ring, and planned a wedding at the hospital. Charlie convinced Shawna to see Hilary and she asked forgiveness, but Hilary instead asked her to be a bridesmaid because she was like a daughter to her. Hilary and Devon were married. Afterward she died in his arms. After Hilary’s funeral, a reception was held at Devon’s condo. Shawna spoke, with Shawna calling her a fairy godmother. Phyliss read pages written by Hillary in which Hilary told Shawna to be strong but not silent, saying she knew Devon would take care of her.

Afterward, Shawna attacked Lily, saying, “Don’t pretend you cared. Her death was your fault for running the red light.” Unaware what she had done, Lily was shocked with disbelief. Charlie verified that it was true. Devon spat that he would never forgive Lily. Cane admitted he had made Shawna keep the secret. Later Shauna tried to leave the condo, but Devon asked her to stay, and her parents were okay with her staying. Devon was insistent on giving a statement at her trial to condemn Lily to make her pay for the death of Hilary and their baby. Neil, Abby and Nate tried to talk him out of it, reminding him that Lily’s children would suffer. Devon gave his statement, asking for the maximum penalty, reminding them that Lily always hated Hilary, and had plotted before to get her out of his life. Shawna testified about witnessing the accident and all that Hilary had done for her, and how much she had lost. At sentencing, Devon recanted his statement and asked for lenience, Shawna asked as well. Lily was sentenced to two years with her driver’s license suspended, a fifty thousand dollar fine, and twelve months in Walworth state prison. Lily went to prison, and spent her first days sobbing constantly. Mattie was arrested for protesting Lily’s incarceration by chaining herself to the prison gate. The family seemed to be falling apart without Lily. Then Lily was targeted by other inmates for coming to the defense of Mikayla whom they were picking on. Lily was put in isolation for her protection, then transferred to Lakewood Correctional Center which was four hours away. Neil moved to Lakewood to assure Lily that family would be nearby. Devon bought him house there and arranged tele-commuting from the company.

Meanwhile Devon surprised Shawna by remembering her 18th birthday. Devon threw her a party, and gave her a four-year college scholarship, all expenses paid, to anywhere she wanted to attend. But Shawna moved to Colorado to join her family when she became afraid of all the strange friends Devon became involved with, the wild parties with drugs, as he attempted to get over the death of Hilary. Charlie was so upset that he had a few drinks. Being underage and drunk, Reed, whose license was suspended, drove Charlie home in Cane’s car during a bad snowstorm, hitting a tipsy Nikki Newman. Scared, they left the scene not knowing what they had hit, with a dent in Cane’s car. Charlie was busted by Cane for drinking. Charlie explained about Shawna and that he had not driven. Reed finally confessed to Victoria, that he was Nikki’s hit and run driver. Victoria and Cane took Reed and Charlie to a recovering Nikki to confess. She surprised them with a confession of her own, that she had been drunk, and felt it was her fault walking in front of their car. They agreed to never tell and ruin the boy’s lives. Cane took Charlie’s license away for the rest of the school year, and put him on a strict curfew.

The twins realized that something was going on with their parents. Cane was suddenly no longer visiting Lily, and they feared they would divorce. They were reconciled with it, seeing first hand the pain they both caused each other. Plus Lily reminded them that they would be leaving home for college soon anyway.

On April 23, 2019, Lily was released from prison, and Neil was there to welcome her. They traveled to Genoa City to attend the grand opening of Society, a new restaurant venture by Devon and Abby Newman, featuring head chef Lola Rosales. Neil felt exhausted and laid down for a nap upstairs at Devon’s penthouse, promising to meet them there later. When Neil failed to show up, Devon went home to check on him. Devon came down his stairway in tears, having discovered that Neil had died of a stroke in his sleep. Family and friends gathered for Neil’s funeral in tears, where Ana sang “Amazing Grace”. They shared remembrances and stories of how Neil had touched their lives and made them better.

Lily and Cane divorced, and Lily returned to Lakewood to continue teaching at the correctional center as an employee. Neil’s will was read a month later by Michael Baldwin. Neil wrote that Cane had hurt Lily but also gave her a lot of happiness and him two grandchildren, so forgave him. Lily was willed Neil’s entire financial assets, trust funds for Charlie and Mattie, Neil’s hope that they would in the future run Hamilton Winters together, and a copy of Hans Christian Anderson Fairy Tales, telling Lily to “go find your happily ever after.” Charlie left for an internship in New York City.

Mattie and Charlie visited Cane in Europe for the 2019 holidays. Devon visited Lily at Christmas, since Elena was working. Lily announced that she had begun dating again.

In 2020, Charlie moved to New York City to take an internship with a producer.

Mattie and Charlie spent the 2021 holidays with Cane and Sam in Hawaii.