Britney Spears' Sons Reunite With Jamie Lynn Spears' Daughters in Sweet Cousins Photo

All of the "lasts" have begun for Jamie Lynn Spears' oldest daughter, Maddie, 17, who just began her senior year in high school.

And she has her family standing proudly by her side.

Maddie posted a series of images from her softball team's "senior night" on Instagram on Sept. 18. Among photos with her friends and family, one image stands out: a snap of Maddie and her younger sister Ivey with their older cousins Sean Preston, 19, and Jayden James, 18, Britney Spears' children with Kevin Federline.

It was a special moment to have the cousins together, especially since the boys have been living with their father and his family in Hawaii since 2023.

Britney Spears' sons pose with her sister Jamie Lynn's daughters in an Instagram photo. @maddie2watson via Instagram

Maddie also shared a sweet family photo with Ivey, Jamie Lynn, and Jamie Lynn's husband, Maddie's stepfather, Jamie Watson. Spears shares Maddie — who uses Watson's last name on social media — with ex-fiancé Casey Aldridge.

Jamie Lynn Spears celebrates her daughter Maddie's senior year in an Instagram post. @maddie2watson via Instagram

Last November, Jamie Lynn reflected on the public criticism she faced when she gave birth to Maddie at just 16 years old.

"I can remember it like it was just yesterday, as the whole world watched and judged as I made the choice to have my baby at 16 years old," she wrote on an Instagram post at the time. "Fast fwd to today, and that same little baby girl is now 16 years old herself announcing that she will be going to play D1 ball for an amazing college."

From the images, Maddie certainly seems close to her softball teammates, even though an injury derailed her senior year.

In one of her first posts on her YouTube channel, Maddie said she initially injured her shoulder when she tore her labrum during a softball tournament last fall. She received surgery for the injury and continued playing after she recovered.

But during the last tournament of the summer's season, she injured her shoulder again. She wears a black arm sling in recent Instagram photos.

"God has a plan. Maybe this was him telling me 'You need to slow down,'" she said in the YouTube video. "He knows exactly what's best for me, and I don't have to understand it."

Despite the injury, Maddie still plans to attend the University of Southern Mississippi and play Division 1 softball next fall.