In a situation where we are speaking of a cybernetic bear in a fight between an ensemble of 40 machine-raccoons, I would argue that the ensemble of machine-raccoons would win. The cybernetic bear would most likely have a difficult time fighting off the machine-raccoons, especially because a machine-raccoon is much faster than a bear, and they would be coordinated in their attack due to their advanced AI.
But before we get ahead of ourselves, let me give a full explanation of the scenario and environment in which such a combat would take place. First, let us consider a fair territory for this event to occur: a stadium or coliseum of some kind. It is important that such a fight take place on flat, solid ground, as the raccoons possess an unfair advantage because of their superior burrowing skills whereas the bear possesses an unfair advantage at altitudes and in climbing trees. The flat arena also prevents the raccoons from hiding in any burrows they may dig and gives the bear a fighting chance to climb a tree to escape the arena. We will also be sure to specify that this is an unattended event, as the cybernetic bear, which still retains its biological faculties, would be distracted by a large crowd cheering it on or booing it and its opponent. Now that we have found a fair territory, let us analyze both the bear and the machine-raccoons.
The cybernetic bear is a powerful creature created with the fusion of machine and beast. It weighs around 2400 pounds and has 20 times the strength of an average man, can run at 40 mph for short periods of time, would be specialized in close-quarters combat, can climb trees, and can dig tunnels. In addition, it is armored with a metal casing and synthetic muscles to enhance its durability and can be upgraded with equipment such as night vision or a gas mask. The bear is intelligent, can be tamed or programmed with specific actions in battle, and will follow orders from its trainer. It is also mounted with an automatic 40mm grenade launcher which, for the sake of fairness, would be armed with 4 40mm grenade canisters. In addition to this, it is also armed with a large-caliber automatic rifle that fires armor-piercing bullets, which would also be equipped with 4 magazines. This bear is designed to be used as a military mount, police companion, or defensively as a guard bear. However, we must keep in mind that the bear is merely cybernetic, and therefore retains many of its biological weaknesses. It can still feel pain, suffer from exhaustion, and has biological functions such as hunger and sleep deprivation, all of which can affect its performance in the arena. We may assume for the sake of this argument that the bear is well-rested and well-fed, but is not so well fed that it would become sluggish due to digestion (even so, its stomach would obviously be enhanced with a reinforced lining, to withstand the rigors of combat). We also have to take into consideration that the bear may have a will of its own, although this is unlikely to go awry as it is specifically trained for the arena. In any case, we can be fairly certain that the bear cannot be tamed by an average man, and would only follow orders from someone with proper training. While this should not be an issue, as I am confident that we could find a proper trainer for the cybernetic bear, it is certainly worth mentioning.
Now, we must consider the ensemble of 40 machine-raccoons. These creatures do not possess an animal mind, rather they are directed by a collective AI server which is in control of their movements. The AI is not sentient, rather it runs off of logical commands and algorithms. As such, it cannot be reasoned with or purposefully outsmarted. It is worth noting that this AI is prone to failure. The more complex an AI, the greater the possibility of a bug or other critical failure in its code. It is worth mentioning that this particular AI has not been used in the arena before, and so its code may not have fully been tested. As for anatomy of the machine-raccoons, they weigh 80 pounds each, collectively weighing more than the cybernetic bear altogether, and are covered with a layer of synthetic muscle and light-weight metal plating. The bear is obviously an offensive weapon, while the machine-raccoons are more utilitarian, although certainly not incapable of defending themselves (their mechanized jaws possess a powerful bite-force that could rival a small alligator). It is worth considering that the machine-raccoons are smaller and thus able to navigate pathways that the cybernetic bear would find impossible due to its size. While we are dealing with a flat terrain, this could still be a useful trait when we consider the coordination of advanced attacks that the machine-raccoon's AI would be attempting to direct in order to tactically defeated the cybernetic bear. Due to the machine-raccoons AI directing them, they would be able to quickly and effectively flank the bear from various angles, although this may not only be from ground level. The bears artificial muscles do enhance its strength and reflexes, but these capabilities could potentially be overwhelmed by the tactical mastery of the collective consciousness of the machine-raccoons.
Now that we have fully considered the aspects of both creatures, I will trace out how I believe the fight would proceed. Again, we are considering a fight between a single cybernetic bear and 40 machine-raccoons in a large, flat terrain within an empty arena. We will assume these two sides begin the fight at opposite ends of the battle-space. At the beginning of the fight, I believe the cybernetic bear would take advantage of its superior weaponry in an attempt to quickly annihilate them with its rifle and grenade launcher as quickly as possible. The range capabilities of the weapons are certainly large enough to hit most of the raccoons, although there is no possibility that all of the machine-raccoons would be destroyed before physical contact. I can see the advanced targeting systems of the cybernetic bear allowing it to destroy a third of the raccoons before they make contact with the bear. This hampers the overall capacity of the machine-raccoon force, but certainly does not destroy them. The machine-raccoons upon making contact with the bear would be primarily focusing their attacks upon the most vulnerable and vital areas of the cybernetic bear, such as its eyes, genitals, and sensors. Once physical contact is made, the fight would rapidly begin to shift. The machine-raccoons would be able to leverage their superior ferocity and combined weight to topple the bear. As the machine-raccoons overwhelm the cybernetic bear, they would proceed to tear it apart limb from limb. The machine-raccoons, with their superior AI, would know exactly what weak-points would be best to target, effectively bypassing the extremely tough armor of the cybernetic bear and getting down deep into the armor to destroy the organs within. Given their numbers, they would be able to tear the cybernetic bear apart. Of course, the machine-raccoons would sustain tremendous losses, but because they are AI-directed, they would not experience fear or a lack of confidence, as the toppled bear would begin to experience as it is overwhelmed by grabbing claws and small bites.
The main reason why I argue that the machine-raccoons would win is because of their superior numbers and coordination. There are simply too many of them to be defeated by a single cybernetic creature, even one with the capabilities of the bear. In such a scenario, I predict that the cybernetic bear would be massacred and around 23-27 raccoons would succumb to their injuries. The remaining force of machine-raccoons would continue to be directed by their AI, and would begin hunting down any humans within the compound. The victors of this battle are obvious. The bear has simply been outclassed by the technology and numbers of the machine-raccoons. The cybernetic bear has been torn apart, with many of its vital organs and wiring exposed for all to see. It would surely be an incredible bloodbath to witness, and I am quite sure that the small, bandit-faced creatures would prevail after a tough struggle.