Longtime friends, former collaborators and one time lovers.

Drake and SZA’s relationship is under the microscope once again as the “Kill Bill” singer, 35, performs at the 2025 Super Bowl Halftime Show — and later goes on tour with Drake’s rival, Kendrick Lamar.

Likely an even closer pal of SZA’s, Lamar, 37, walked onto the field at the Caesars Superdome in New Orleans for the Kansas City Chiefs’ face-off with the Philadelphia Eagles just days after his Drake dis track “Not Like Us” earned him five Grammys.

Here’s a timeline of what you need to know about SZA’s relationship with 38-year-old Drake.

Drake and the R&B singer — whose real name is Solána Imani Rowe — dated for an unknown period of time either in 2008 or 2009. It wasn’t until a decade later that Drake revealed the pair had a romance.

On Oct. 2, Drizzy releases “Mr. Right Now” with Metro Boomin and 21 Savage, which features a line revealing that he and SZA used to be an item. Referring to an unnamed woman, Drake sings, “Yeah, said she wanna f–k to some SZA, wait / ‘Cause I used to date SZA back in ’08.”

The “Normal Girl” singer posts on X (formerly known as Twitter) on Oct. 4, confirming the pair dated.

“So It was actually 2009 lol,” she wrote. “In this case a year of poetic rap license mattered. Lol I think he just innocently rhymed 08 w wait. Anybody who really knows me and was around during this time can confirm.”

She added, “it’s all love all peace.”

The now 35-year-old siren went on to explain that she weighed in because she wanted people to know she was not underage when they dated.

“I just didn’t want anybody thinking anything underage or creepy was happening,” she posted. “Completely innocent. Lifetimes ago.”

After appearing as the musical guest on an episode of “Saturday Night Live” that also featured a sketch lampooning Drake as a womanizer, SZA compared the “Hotline Bling” hitmaker to Regina George from the movie “Mean Girls.”

“In a strange way, I was like, ‘Did they know?’” she told Audacy, recalling how she wondered whether “SNL” writers knew she and Drake dated. “But they didn’t ask me to be in it. Nobody said anything.”

She added, “I feel like Drake has a Regina George quality to him where it’s just kind of like, ‘Have you or anyone you know been personally victimized?’ He’s like a cool kid, you know.”

“When you’re the popular kid in school, it’s entertaining. It’s entertaining, but you sometimes are taking losses in the midst of that entertainment. The honesty, I respect that. But I definitely laughed real hard…I cackled,” she noted.

Of her friendship with Drake, SZA said, “We’re cool. And we’ve always been cool. It’s never been weird.”

The “Nobody Gets Me” singer also said that Drake gave her a heads up that he was mentioning their past relationship in “Mr. Right Now.”

“It didn’t come completely out of the blue when he let me know,” she added. “I didn’t know it was a song with 21 [Savage] or anything like that. But anytime he’s ever mentioned me, it’s always been positive. He’s never said anything negative about me. I’m grateful for that. I think highly of him … He’s King Drake.”

Drake and SZA joined forces for their first ever collab in 2023, working together on two tracks off his “For All The Dogs” album, “Slime You Out” and “Rich Baby Daddy.”

SZA downplayed her and the “God’s Plan” rapper’s romance in an interview with Rolling Stone.

“We were really young,” she said of her and Drake’s fling. “It wasn’t hot and heavy or anything. It was like youth vibes. It was so childish.”

In an Oct. 30 interview with The Wall Street Journal, SZA said she thought Drake was trying to “sabotage” her by using the first draft she sent him of her feature for “Slime You Out.”

“I just handed in the first draft to Drake, and he’s putting it on his album,” she told the paper. “I’m scared because I handed in second vocals and he didn’t use that. And now I’m like, ‘Are you trying to sabotage me?'”

“I know that’s not true. I literally know that’s not true, but that’s how bad I feel about my first draft. When things come from an effortless space, I almost can’t enjoy it,” she added.

Just as Drake’s feud with Kendrick Lamar was heating up, SZA got embroiled in the beef. On April 13, a leaked demo of Drizzy’s K-Dot dis “Push Ups” circulated online. On it, the Canadian hitmaker asserts that SZA is more deserving of being in rap’s “Big 3” than Lamar.

“Pipsqueak, pipe down / You ain’t in no big three, SZA got you wiped down,” Drake spits. “Travis [Scott] got you wiped down, [21] Savage got you wiped down / Like your label, boy, you in a scope right now.”

Within less than 24 hours, SZA responded on her Instagram Story, posting a clip of NeNe Leakes at one of the “Real Housewives of Atlanta” reunions, asking in exasperation, “Now why am I in this? You see how I get thrown into it? I ain’t even did nothing.”

Months after the Kendrick-Drake feud reached its zenith with Lamar releasing “Not Like Us,” SZA featured on two tracks off K-Dot’s new album, “GNX,” “Gloria” and “luther.” Though they collaborated as far back as 2014, this is the first time they worked together since Lamar and Drake’s feud reached a boil.

On Dec. 3, SZA was announced as Kendrick Lamar’s opener for his upcoming Grand National Tour, which kicks off its 19-city, three-month run in April.

While appearing on an episode of “Hot Ones Versus” to promote her new movie “One of Them Days” alongside producer Issa Rae and co-star Keke Palmer, Palmer asked the “Kill Bill” singer whether Drake was a good kisser.

“That’s why I said f–k you in advance,” SZA told the “Nope” star, refusing to answer the question.

“We were children!” she said. “We were children. 2009? We were children.”

Palmer prodded her, saying the question was a “simple good or not good,” with Rae adding it was “really easy.” The “Insecure” creator continued, “And the fact that you don’t want to say one is very telling.”

“Y’all trying to double-team me into guilt ‘cause you know I’m affected by it? F–k y’all,” SZA replied.

On Jan. 23, Kendrick Lamar revealed that SZA would be joining him at the Caesars Superdome in New Orleans for the Apple Music Super Bowl Halftime Show.

The pair shared a teaser to their respective Instagram accounts showing Lamar on a football field talking with someone on his cell, saying that he’s “been thinking about a guest performer” for his set.

SZA then sneaks up behind him and douses him with what looks to be blue Gatorade.