FinalFantasyFanAeCK
Ummm...If you use Cloud, you could try the following combination to win
Weapon: Ultima Weapon (if you don't have Ultima Weapon, any strong weapon will do with a lot of slots)
Armor: Tetra Elemental(or any armor that absorbs elemental attacks)
Accessory: Ribbon (It can stop some of the side effects of the slot machine, like mini, frog, and poison.)
Materia Slot (for weapon):Added Effect-Contain, Time, Counter, Slash-All, and Sense
Materia Slot(for armor): Final Attack-Revive, Deathblow, Cure, Barrier, and Odin(optional)
It works for me most of the time as long as you don't get that slot effect that makes your Accessory working, or your magic stop working.
If battle square is hard for him, I doubt that he has the final attack materia.
My advice is avoid materia at all costs, because the best handicaps (the ones that give you the most BP) are the materia breaking ones. Equip your best weapon, your best armor and a ribbon. The ribbon is an absolute must. Also, dont be afraid to quit, because some BP is better than none. Stop if your HP gets halved below 1000 or if your speed is halved.
The only materia I equiped was restore (because regen works VERY well, try it out), HP Plus materia, counterattack and 2x cut. Hit fast and hard, and cure yourself (again, regen FTW).