Matthew Stafford’s wife Kelly shares ‘sad’ message as she misses gal-pal time with Cooper Kupp’s wife Anna

Matthew Stafford’s wife, Kelly, has been a longtime friend of Cooper Kupp’s wife, Anna. During Kupp’s stint with the Los Angeles Rams, Kelly and Anna have often been spotted cheering for their husbands together. Recently, the gal pals reunited for a tennis session, a glimpse of which Kelly shared on her Instagram.

On Saturday, Kelly Stafford reshared an Instagram reel from “D&D Tennis,” which featured a clip of her practicing at a tennis court with Anna Kupp. The duo visited Malibu Racquet Club in Malibu, California. Along with the reel, the Instagram story featured Kelly’s emotional message for Anna.

“@annamariekupp Makes me happy and sad at the same time. Offseason 2026 can’t come soon enough (for non football related reasons),” Kelly wrote.

Matthew Stafford’s wife Kelly shares ‘sad’ message for Cooper Kupp’s wife Anna (Image Credit: Kelly/IG)

Before sharing a rare glimpse of her fun time playing tennis with Anna, Kelly informed fans about a health setback on Tuesday. The podcaster posted a photo of her arm, with a medical drip attached, on her Instagram story. While she didn’t share many details about the health issue she faced, Kelly mentioned:

"Fine, but damn, I have felt better.”

Matthew Stafford’s wife Kelly opened up about possibility of relocating from California

Amidst constant buzz around Matthew Stafford’s post-retirement plans, his wife, Kelly, shed light on the couple's relocation plans. In an episode of “The Morning After” podcast last month, Kelly explored the possibility of their family leaving California for an unknown Southern city.

“I'm having a little trouble, like, what do we do when Matthew's career is over?” Kelly said (Timestamp - 7:51). “I find the South a home. Right. There's a lot to it that I love. But then I think about out here and how great it is and how my kids love it here (California), and there's part of me that wants to stay.”

While there hasn’t been a lot of clarity around Matthew Stafford’s retirement plans, Kelly has certain things planned for herself. The podcaster previously revealed her plans to pursue a sports-centric career after the Rams quarterback retires from the NFL.

Apart from football, she often talks about her personal life with Matthew on her podcast. In an episode from earlier this month, Kelly spoke about signing a prenup with the Super Bowl champion.