I had a similar problem - id charge the battery, run the tractor and it wouldnt start- turns out it was a bad diode from the stator charging wire - sucked the juice from the battery instead of charging it. New diodes can be bot for like $1 at radio shack - make sure its a 12volt type.
Id also check the starter like Mickey said- they can eventually draw a ton of amps when they start to wear out or get dirty -ive managed to 'restore' a couple of my briggs starters by pulling them apart,spraying the whole thing with carb cleaner, cleaning the armature with sandcloth and cleaning the contacts ( or you can replace them) - most briggs starters are easy to take apart n clean- IF they have an open end - ive used small L shaped pieces of wire to hold the contacts back while reassembling the starter - its worth a shot then paying $100 for a new starter.
A few of my tractors also tend to drain the battery while sitting , as wjjones mentioned - i simply unhook the battery when i park it.
Another thing to mention is what brand of battery are you using? A cheep low CCA battery or a high end high CCA battery? No matter what tractor you own, i always go with a good quality high CCA ( cold cranking amp) battery - low CCA batteries can be easily drained just starting them ( been that route- just wasting money)- high CCA batteries wont hurt the tractor, if you think it might- upgrade the battery cables to heavy duty type.
My one 90's craftsman GT5000 specifically states on the battery cable to use no less then a 600 CCA battery.
Another thing is when you buy the battery, insist on having them test it for voltage, sometimes theyll hand you a 3 year old brand new battery thats sat there in the shop all discharged before buying it - it probably wouldnt hurt to throw it on the charger either when getting it home for a bit to top it off.
Hope this helps you out.