Wimbledon has never needed a script, but this year it has more material than usual to work with. Serena Williams is back competing in Grand Slam singles for the first time since 2022 and playing doubles with her sister Venus. The defending men’s champion, Jannik Sinner, arrives with more questions than answers after wilting at Roland-Garros in May. And somewhere between the double-digit withdrawals, the injury-compromised entrants, and the looming heat expected to return midweek, the All England Club is reminding us that the grass-court season is chaos in a white dress code.

With action kicking off on the pristine lawns of Wimbledon on Monday, June 29th, what follows is Court Theory's guide to the fortnight — the questions worth asking, the matches worth watching, and the things that may not go according to plan.

1) How will Serena Williams fare at Wimbledon? Thanks to the final women’s wild card, for now, this is the question of the tournament. That’s in part because everybody wants to know how the GOAT will size up four years after retiring. After all, we haven’t seen her compete in singles since announcing her return to the game. She’ll face Maya Joint, who is just inside the top 100, in the first round on Centre Court on Tuesday. With all of the attention surrounding those developments, it could be easy to forget that Serena and Venus are playing doubles together for the first time since Serena’s retirement, which should also be great fun.

2) Can Jannik Sinner beat the heat? The world number one and defending champion enters Wimbledon seeking his fifth major as the favorite, but some doubts are at play. Between his ongoing fitness issues when facing the heat (which is expected to reappear in the second half of the week in London) and having skipped the grass court warm-up tournaments this year, Sinner’s lead-up to Wimbledon has been less than ideal. The last time he played a match, he wilted up 6-3, 6-2, 5-1 against number 56 Juan Manuel Cerundolo to lose in the second round of Roland-Garros. With so much on the line at SW19, it seems odd to leave that as your most recent competition memory.

3) Can Iga Swiatek possibly defend her title? We’re not saying it’s impossible, but the signs aren’t exactly in her favor, either. The world number three hasn’t won a tournament this year, and in her only grass tournament, she lost her first match to Emma Navarro as the number one seed. And, if that’s not enough bad news for the defending champ, she’ll be tested immediately by Taylor Townsend, a player whose game is well-suited to the surface. If they both get there, an Iga-Serena match is waiting in the third round.