So I've been experiencing a weird pain on the top of my left foot at the ankle (basically the opposite side of the Achilles tendon).  There are a couple tendons there that feel tender and sore when I rub them.  I sometimes experience a sharp pain when planting (I plant my left foot to jump) or when landing, but most of the time it isn't noticeable.  I don't remember injuring it..just one day it popped up when I was working out and it has lingered for the next month.  It definitely isn't getting worse but I'm not sure it's getting much better.  During normal walking or jogging I don't feel anything, it only pops up when I try to be explosive off my left foot or when I'm stretching my foot outwards.

Could this be an issue with my shoes?  Do I need more arch support?  Anyone else experience something like this?

Yeah.  I can't bend my knee too far forward without it hurting the front of the ankle. 

Any suggestions on how to deal with this injury?

not me i still have that pain when i do that exercise or try to get a lot of dorsiflexion