Alright, let's try this again...
Miles "Tails" Prower
vs.
Fox McCloud
Physical Ability
On Fox's end, while he usually relies on his blaster, he's got a pretty solid grasp of martial arts, seeming to favor kicks. He is also somewhat adaptive, in Starfox Adventures he becomes pretty proficient in using Krystals staff after having it for a short period of time. That said, his fighting style, otherwise, seems to favor many rapid attacks over brute strength.
Tails, on the other hand, has shown relatively little actual style, although that's not to say he is afraid to throw a punch, but his odd fighting style seems to balance between punches and kicks while also using his tails as weapons at times, and with good reason, as he has shown to be able to break steel cages with them. Like Fox, Tails seems to otherwise favor speed and agility. With, and sometimes without, the assistance of his tails, he has been able to keep up with his hero Sonic whilst running at high and super-sonic speeds, and has shown great reflexes and agility. While his tails are strong, the rest of his body could be limited in power by his age (Let's go with the average of the video game age of 8 and the comic age of 11 and say he's about 9 1/2), however, the addition of his extra two extremities to a combination of punches and kicks can make him a bit harder to predict.
Special Abilities
Fox's speed has some cool additions. He is able to move at incredibly high speeds, leaving an afterimage and plowing through anything in his path. However, this is only usable in short bursts. He is also able to use his Fire Fox ability, cloaking himself in flames and dashing at an opponent.
Tails is able to use his tails to either fly or glide, depending on his situation, although this ability tires him out quickly. It should also be noted that, between him, Sonic and Knuckles, he seems to be the only one who can swim. Tails is also able to assume a Super Tails form, making him temporarily invincible and granting him four "Super Flickies", which automatically seek and destroy nearby enemies, but due to his young age, this is exceedingly difficult for him.
Handheld Gadgets
Fox is rarely seen without his blaster. A small arms laser, it has no limit on ammo and is capable of rapid, semi-automatic or fully automatic fire, but has a limited range of which the laser bolts peter out into nothing. Fox is also armed with a reflector shield, able to send projectiles back at their users and damage those who get too close.
Tails, despite his status as genius and inventor, rarely carries much around if he doesn't know he'll need it. He does, however, carry around a large amount of ring bombs that he can scatter from flight or throw with a lot of power and relative precision. The actual explosive range of these bombs is pretty small, although still rather strong.
Transports
Fox flies the Arwing, a small, personal flight ship capable of flight and space flight armed with laser canons and single lock Smart Bombs that have some great destructive power. The Arwing is well armored, able to withstand blasts and bombs and continue into battle. He also has the Landmaster, which is powerful and well armored, but slow and somewhat cumbersome.
Tails' main trainsport is the Tornado 2/Cyclone, a transforming car/plane/jet/mech-walker. In plane or jet mode, the craft is armed with multi-lock homine missiles and a gattling gun. It is fast and maneuverable, obviously moreso in jet mode. In walker mode, it keeps these weapons and while it slows, it does become more maneuverable as the cockpit and weapons can rotate on the legs a full 360 degrees. The walker is also able to hover for short distances and has been equipped with a large laser canon, whose beam is about as wide as the Cyclone itself. In spite of this, the armor of the Cyclone may be somewhat weaker and the way he rides, Tails is always exposed.
Mentality
Fox is a seasoned soldier and mercenary. But while experienced, he also seems to be more of a doer than a thinker at times, ready to fight and sometimes having a short temper.
Tails is a genius mechanically, but, to my knowledge, has not translated that into strategical genius. Young and sometimes naive, Tails can tend to more over think things sometimes and become frightened, but he has mostly grown out of that.
Now then...
Who Would Win