Norman Reedus's Daryl Dixon has been a staple of The Walking Dead for all of the show's 11 seasons, remaining a fan-favorite character throughout his time on the series. Daryl continues to headline the show as the benchmark zombie series airs its final episodes this year.
In his time fighting for survival in a post-apocalyptic world, Dixon has fallen victim to several vicious characters along the way, any one of which would have sooner seen him dead than live peaceably. Some of these characters truly made an impact on Daryl, becoming his greatest enemies of all time.
Gareth
Gareth was the cruel and uncaring bookkeeper in the cannibalistic community known as Terminus, which captured Daryl and his friends at the end of Season 4. This predator kept the group locked away before priming them to be slain, butchered, and eaten by the people of his community.
Though Gareth's community fell at the hands of the survivors, the cannibal still saw it fit to pursue the group in an attempt to win his revenge. Haunting the group for several episodes, Gareth would eventually make it absolutely necessary for Daryl and his friends to put the surviving Terminites to permanent rest.
Leah Shaw
Leah has the notable distinction of being Daryl's first bonafide love interest in the series, after ten years of the character remaining, for all intents and purposes, single. However, the two were torn apart by time and circumstance, never able to rekindle what they had once had upon their eventual reunion.
After finding each other once more, it became clear that Daryl and Leah's past was irreconcilable, especially given her new affiliation with Pope and his men. Since their defeat, Leah has an even larger ax to grind, making the divide between the two something that will need to be resolved before The Walking Dead ends later this year.
Merle Dixon
At the outset of the zombie apocalypse, Daryl Dixon only had one person who he cared about: his older brother Merle. The two would survive the first few months of the apocalypse together until they eventually found themselves on opposite ends of a war between two communities of survivors.
Though Merle was one of Daryl's best friends, he was certainly also one of his greatest enemies. Even before ing the Governor at Woodbury, Merle proved to be a negative influence on his younger brother, encouraging the obnoxious and boisterous behavior that he himself fostered. Much of Daryl's arc in the series has involved his moving past the influence of his brother to become his own person.
Pope
Pope served as the primary antagonist of the first third of The Walking Dead's final season, commanding a group known as the Reapers, who wiped out entire communities and claimed to be doing the work of God. Daryl, alongside Maggie, would eventually lead a contingent of Alexandrians to take down Pope and his Reapers for good.
Pope proved to be a formidable force of evil, attempting to ingratiate Daryl into his group so that the Alexandrian would assist him in his dastardly deeds. The post-apocalyptic tyrant proved far too brutal for Daryl's sensibilities, however, leading to his own demise at the hands of his top lieutenant Leah, who he had ordered to kill Daryl's friends.
Simon
Simon was the top lieutenant under Negan, commanding the Saviors at their home base, Sanctuary. He often served as the face of the organization, demanding tributes from the cooperating communities under the Saviors' rule, but eventually proved too ambitious for his own good, leading to Negan taking his life.
The series drew a distinct parallel between Simon and Daryl at the former's introduction, as both served as the right-hand man of their respective leaders. However, it quickly became apparent that Daryl was far more loyal to Rick than Simon was to Negan, proving Dixon's superiority over the Savior commander.
Alpha
After the imprisonment and subsequent redemption arc of Negan, Alpha filled the show's gaping baddie hole quite nicely as the tyrannical leader of the Whisperers, a group of survivors that wore the skin of the very dead that destroyed the world. Indeed, Alpha's mysterious backstory and sadistic tactics make her a perfect character to appear in the spinoff anthology series Tales of the Walking Dead.
Though Alpha was always more-or-less drawn to conflict with Carol Peletier, she served as a major thorn in Daryl's side during her time in the series as well. Daryl took issue not only with her community's aggressions but also with her abuse of her only daughter Lydia, whom Daryl had come to befriend. Their rivalry came to a head with a vicious one-on-one battle that nearly left both of them dead.
The Governor
The Governor was the first truly evil villain who, though conflicted at times, wreaked more havoc than any other prior antagonists in the series combined. Blinded by his sheer hatred for Rick and his group of survivors, the Governor refused to rest until he had killed them all.
Daryl held a special animosity in his heart for the Governor after he killed Daryl's older brother Merle. After Woodbury's fall, Daryl would Michonne in routine hunts for the escaped villain for months before eventually giving up. Of course, their failure to find the Governor would result in one final battle that would leave their beloved prison community destroyed for good.
Dwight
Dwight is a former member of Negan's Saviors who betrayed the group in order to help the coalition of communities led by Rick defeat the post-apocalyptic dictator and reestablish their own world order. However, before his redemption, Dwight proved to be a fairly heinous villain in his own right.
Daryl fostered a special hatred for Dwight after he and his wife Sherry conned him and stole his motorcycle, jacket, and crossbow before leaving him for dead in the woods. And, with Dwight murdering Denise in cold blood using Daryl's iconic weapon, as well as personally shooting and torturing him, it was all Daryl could do to not kill the Savior himself at the first chance that he got.
Negan
For much of The Walking Dead's run, Negan has been presented as the show's primary antagonist. He and his Saviors wreaked havoc on Daryl's friends in ways that no one ever had before or ever would again. As such, he became the personal enemy of every single one of his oppressed communities.
Negan always took a sadistically inclined notice of Daryl, longing to either recruit him to the Saviors or have him killed, a streak of villainy which Daryl would not forget, even long after Negan's redemption arc had begun. Now, with bigger enemies on the horizon, whether or not he remains one of Daryl's enemies is something Negan will have to work out before the end of The Walking Dead.
Beta
Beta was the massive, brooding, and silent lieutenant to Alpha. After his superior's death, however, Beta would take control of the Whisperers for himself, leading them in an all-out assault on Alexandria using their army of walkers to tear the community to the ground.
Daryl and Beta came to blows on a number of occasions over the latter's short time on the series. With Rick's departure from The Walking Dead the season prior, Daryl had become the best-equipped hero to take on such a massive threat, eventually landing the fatal blows to the Whisperer that would lead to him being devoured by his own army.