Inside Kelly Osbourne and Sid Wilson’s Relationship Timeline
Ozzy Osbourne’s daughter, Kelly Osbourne, has officially ended her engagement with fiancé Sid Wilson as of March 2026. Kelly has been the subject of intense scrutiny before and after her father’s death. Now, fans are looking for the reason behind her and Wilson’s breakup. Here’s what to know about Kelly and Wilson’s relationship timeline, from their initial friendship to the end of their romance.
Kelly Osbourne and Sid Wilson reportedly first met in 1999 and began dating in 2022
Sid Wilson is a musician best known as the longtime turntablist for the Grammy-winning heavy metal band Slipknot. He performs under the number “#0” and contributes scratching, sound effects, and the chaotic audio textures that define the group’s sound. The musician was born in Des Moines, Iowa, in 1977, and he joined Slipknot in the late 1990s as the band was gaining momentum.
His story with Kelly Osbourne began in 1999. According to People, the two met when his band first toured with Ozzfest, the music festival that Sharon and Ozzy Osbourne founded. In 2022, a source confirmed the couple was dating.
“Kelly and Sid met when his band was touring with Ozzfest in 1999,” the source claimed. “They have remained friends since. They are very happy together.”
Kelly then announced her relationship with Wilson in a Valentine’s Day Instagram post in 2022. She posted a carousel of photos of her kissing and smiling with her then-boyfriend. “After 23 years of friendship I can’t believe where we have ended up!” she captioned the post. “You are my best friend, my soulmate and I am so deeply in love with you Sidney George Wilson.”
Kelly Osbourne announced her pregnancy in May 2022
Shortly after hard-launching her romance, Kelly Osbourne took to Instagram to announce that she and Sid Wilson were expecting.
“I know that I have been very quiet these past few months so I thought I would share with you all as to why … I am over the moon to announce that I am going to be a Mumma,” she wrote, according to People. “To say that I am happy does not quite cut it. I am ecstatic!”
Wilson also posted an ultrasound of the baby in 2022. He captioned the post with a series of heart emojis and no other explanation.
In 2024, Kelly discussed raising her son, Sidney. She explained how her family was “always on tour,” which gave her a “beautiful experience” that she’d like to also give to her child.
“He’ll get to travel the world, meet all sorts of people, get exposure to art and music and science and things he never would see if he wasn’t traveling the world,” she told People.
The couple made a red carpet debut in 2024, followed by an engagement in 2025
In 2024, Kelly Osbourne and Sid Wilson made their red carpet debut at the Grammy Awards. At the time, Slipknot was nominated for Best Metal Performance for “Hive Mind.” According to Entertainment Tonight, Kelly posted photos of herself getting ready on her Instagram Stories. One of the photos she posted shows her and Wilson kissing while they prepped for their red carpet moment.
In 2025, Wilson and Kelly got engaged. Wilson popped the question at Ozzy Osbourne’s final Black Sabbath gig in July. Sharon, Ozzy, and brother Jack were present for the event. A video posted to Kelly’s Instagram shows the proposal, with Ozzy hilariously interjecting, “F— off, you’re not marrying my daughter.”
Kelly Osbourne and Sid Wilson put on a united front into early 2026
Despite Kelly Osbourne’s grief over the loss of her father, Kelly and Sid Wilson put on a united front. In January 2026, Kelly posted a carousel of photos with Wilson to celebrate his birthday. “Happy Birthday Daddy Sid we love you so much!!!!!” she captioned the post.
In October 2025, Wilson also posted a sweet tribute for Kelly’s birthday. He posted a photo of her sitting on a swing attached to a tree with the caption, “Happy birthday to my life, my love, my everything.”
The couple ended their engagement in 2026
An insider close to Kelly Osbourne and Sid Wilson told the Daily Mail that the couple called off their engagement in 2026.
“Kelly and Sid have decided to call off their engagement,” the source said. “Kelly has been struggling following the loss of her father. The grieving process has been incredibly difficult, and she’s been doing everything she can to cope.”
“In truth, she and Sid have been facing challenges in their relationship for some time, and things were not as they appeared,” they continued. “They tried to make it work, particularly for the sake of their child, but ultimately decided that separating is the best path forward. Kelly has endured a great deal over the past year. Despite everything, she remains sober and is now focusing on herself and her role as a mother moving ahead.”
