The order only really matters if they can chalk it up to poison. If Anne and Katherine dye of something obvious and irrefutable in 1531 (smallpox, sweating sickness, horse accidents ect.) then the main response is going to be on both sides of the debate that this is God's punishment. It's not impossible and if you can't look at the deaths as anything else then it truly doesn't matter. What matters is the aftermath.
In likelihood, the Pope immediately goes into reconciliation mode, as do the Hapsburgs, and Henry starts getting offered pretty much every available Princess in Europe to take over as Queen. He's free, fun and forty. Unfortunately, there's very few available, of age Princesses available that make sense. Mary of Austria would make sense except she doesn't want to remarry and no one is forcing her. Eleanor of Austria is recently remarried, her daughter is too young, as are pretty much every Hapsburg related candidates until you start getting into the weeds of people like Marie of Brandenburg-Kulmbach or Maria of Saxony, both way too far removed to count. The only unmarried female Hapsburg is Charles' illegitimate daughter with Germaine of Foix, but she's (a) a bastard and (b) not really acknowledged.
The French can offer Marie of Bourbon and Marie of Guise, but there's not really any major Princesses they're going to give him. Madeleine is too young and fragile, Margaret is far too young. Henry needs a grown woman, not a young Princess. Funnily, Anne and Amelia of Cleves make the most sense if he doesn't want a French bride. Now, that's assuming Henry goes into "get an heir" mode and not "my dead girlfriend" mode. If he goes into full blown mourning, Maria of Portugal is probably going to be the Hapsburg choice, or one of the Danish girls (Christina is more likely as Dorothea is needed to retake/set in stone the Danish stuff).
Outside of marriage stuff, Thomas Boleyn might get his prestige anyway as a representative of the woman Henry lost, and it might be funny if Henry just marries Mary Boleyn because she reminds him of her sister. Or retakes her as a mistress. Also Mary Tudor is likely still legitimate, but you never know with Henry. He might want her declared a bastard just because she represents the stuff that held him back from loving Anne.