Maybe i'm simply trying to do the wrong deke.
It sounds like this is the case. But it's not your fault. It's EA's fault, because the objective is misleading. Even though the objective doesn't say the word "backhand", you need to do backhand toe drag shots. With Hybrid controls you only need to use the right stick to do a backhand toe drag shot. You press the right stick (R3), and while holding it down, you move it backward and then forward. And with Total Control you press and hold the Square button as EA_Aljo said.
EA_Aljo Why does the objective not specify that we need to do backhand toe drag shots? And why didn't you specify it in your comment either? If you look at the controller settings, you can see that a toe drag and a backhand toe drag are two different things. And the objective only says toe drag shots even though you are asking us to do backhand toe drag shots. You gave instructions for the correct deke, so in that sense your answer was good and I hope it helps OP with the objective, but you didn't mention that the correct deke is actually a backhand toe drag. But anyway, if you want us to do backhand toe drag shots, then you should say backhand toe drag shots and not just toe drag shots, because they are two different things. I think I have mentioned this before, but apparently it hasn't been changed. Can you forward the feedback to the team?