Old Man Logan would get one more brawl with a Hulk closer to his age towards the end of his solo series. A version of Maestro that this Logan has confronted in the past, an aged but demented version of the Hulk, arrived in the mainline continuity. He took over a small town and declared himself King. Despite his fading healing factor , Old Man Logan decided to target Maestro and kill him. Things go poorly for Logan initially, with Maestro quickly beating down Logan. As their feud raged on, Logan was almost murdered by the evil version of multiple times in stories by Ed Brisson, Mike Deodato and Ibraim Roberson.
Ultimately though, Logan healed up enough so that he could fully confront Maestro. The final battle was considerably more brutal than any of their earlier skirmishes. Their battle ended with Logan beheading Maestro, while killed the dark version of Hulk. The strain almost killed Logan, who barely healed up good enough to return to his own reality. This means that ultimately, Old Man Logan (barely) has a winning record while against Marvel's Hulks.