Singles : Rih by far
Albums : Britney by far
Impact : Britney
Awards/Acclaim : Rih
Rihanna will be a legend, she has the hits, sales, she only lacks the iconic moments (music related that is, the Chris Brown mess is pretty much a pop culture milestones) which she'll get once she becomes a good performer (she's improving). Britney is a legend.
Britney feels a lot bigger and undoubtedly had the bigger peak/more iconic songs and moments. But Rihanna has much better longevity, I see her career lasting a long time yet whereas Britney at the same point in her career was slipping.