Bonebreaker has a lot of equipment, but Punisher is a lot more agile. Not to mention that the Punisher also received extra powers gained from his bonding with the Venom symbiote at one point. Bonebreaker is strong, but he may have met his match in this round. The Punisher doesn’t go down so easily. Punisher wins.
Bonebreaker is not that powerful physically, but he has a lot of tech to help him out in a long range battle. Barbarus is the complete opposite and he will rely on his close combat skills to win him the round. If Barbarus gets close to Bonebreaker, then it’s all over. I don’t think that Bonebreaker’s guns would hold him off for long enough. Barbarus wins.