Every Big Bad Oliver Queen Fights in Arrow, Ranked

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Before landing on Lian Yu, Oliver Queen, portrayed by Arrow’s character, is not particularly heroic, spending most of his time enjoying the party scene and putting himself first. His disregard for others is evident when he takes his girlfriend’s sister on a yacht named the “Queen’s Gambit,” which later sinks in the North China Sea, resulting in her loss at sea. The island serves as Oliver’s harsh but valuable classroom, teaching him crucial skills like killing and survival. Upon returning to Star City and embarking on his vigilante career, he recognizes his potential to significantly impact his hometown. However, there are some who strongly oppose his methods and would be content seeing him meet an early demise.

During the course of Arrow, Oliver confronts eight major villains, each of whom knows how to provoke him and endanger his loved ones and the city. Despite their differences, it’s relatively straightforward to compare them in terms of their overall impact.

8) The Anti-Monitor

It’s arguably not appropriate to compare the Anti-Monitor with other villains in this list since he primarily belongs to the Arrowverse rather than being tied specifically to Oliver Queen. Nevertheless, he serves as the central antagonist during Season 8, as the Monitor assigns Oliver a task to prevent the Anti-Monitor from destroying multiple realities.

The absence of a deep personal bond between Oliver and the Anti-Monitor weakens the intensity of their conflict, yet there are still compelling aspects. Their battle during the “Crisis on Infinite Earths” crossover is awe-inspiring, and it offers Arrowverse’s founding hero an opportunity to declare, “You have failed this universe!

7) Emiko Adachi

In simpler terms, the character named Oliver’s father, Robert Queen, hides many facts from his son. However, the most significant secret is that he has another daughter named Emiko Adachi. While Oliver resides in a mansion, Emiko lives in The Glades, which fuels her resentment towards her half-brother. In Arrow Season 7, when Oliver gets imprisoned, Emiko sees this as an opportunity to take revenge.

Initially, Emiko appears to take up the mantle of Star City’s latest hero, impersonating the Green Arrow for a while. But in reality, she is collaborating with the Ninth Circle to tarnish Oliver Queen’s reputation. Unfortunately for her, things don’t turn out as planned, and due to the complexity of her reasons, she fails to match up to some of the more memorable antagonists from the Arrow series.

6) Ricardo Diaz

In the sixth season of Arrow, Star City encounters difficult circumstances, with villain Ricardo Diaz establishing a drug enterprise intended to soothe the public’s concerns. Remarkably, even Oliver Queen’s trusted friend, John Diggle, begins purchasing from Diaz, as the substance enhances his strength in combat situations.

Oliver dislikes Diaz’s approach in games, so he confronts him aggressively. Living on Star City streets provides a similar training as the League of Assassins, since Diaz consistently challenges the Green Arrow. Their rivalry is strong, but Diaz crosses the line by resurfacing at the start of Season 7 and attempting to disrupt Oliver’s life again.

5) Damien Darhk

Without a shadow of a doubt, it’s undeniable that Arrow Season 4 falls short compared to its predecessors. The narrative seems scattered, and the characters’ emotions often remain unclear – a challenge not solely borne by Damien Darhk.

Dark once belonged to the League of Assassins, but now he uses magic as his signature move. His powers often frustrate Oliver, and it takes great effort from Team Arrow to defeat him. Yet, Dark’s captivating character doesn’t go unnoticed, as he reappears in Legends of Tomorrow.

4) Malcolm Merlyn

On the television series “Legends of Tomorrow,” it’s announced that another villain from the Arrow universe will make an appearance, this time being Malcolm Merlyn, also known as the Dark Archer. During Star City’s first season, Merlyn plots to demolish The Glades, a neighborhood he feels is causing more harm than good. However, his plan catches the attention of Oliver, who must then face the challenge of battling his friend’s father.

Because Oliver has been friends with Malcolm since childhood, their relationship dynamic is deeply emotional. Moreover, it doesn’t help Malcolm’s situation that he consistently stirs trouble for Oliver – interfering with the League of Assassins and endangering Oliver’s daughter, Thea Queen.

3) R’as al Ghul

In the television series Arrow, the League of Assassins gains its significant presence due to the influence of Ra’s al Ghul. During Season 3, he makes his grand appearance, persuading Oliver Queen to join him, in return for saving Thea’s life. This offer comes after a fierce confrontation between Oliver and Ra’s al Ghul, where Oliver almost meets his demise as the Demon’s Head.

As Oliver is being trained to take over the League of Assassins, he’s also devising a plan to defeat Ra’s. Aware of this, Ra’s continues his pursuit because he believes he can transform Oliver. However, his overconfidence ultimately leads to his demise, causing significant destruction before he meets his end.

2) Deathstroke

Oliver encounters Slade Wilson on Lian Yu, where the ruthless soldier eventually takes the misled individual under his protection. For more than a year, they engage in combat side by side until Slade acquires the Mirakuru serum, causing him to lose his sanity. Ultimately, Oliver is forced to euthanize his friend, but their paths cross again later on.

In Season 2, the character named Slade arrives in Star City with a grudge against Oliver. He carries out his vengeance by murdering Oliver’s mother and deploying Mirakuru soldiers to wreak havoc throughout the city. However, Oliver manages to outsmart Slade thanks to his swift intellect. Later on, Slade reappears and plays a crucial role in defeating an upcoming villain.

1) Prometheus

Similar to other antagonists on this roster, Adrian Chase holds Oliver Queen accountable for the loss of someone dear to him. However, unlike other villains, Chase stands out as the Arrowverse’s most ardent adversary. He consistently torments Oliver and revels in the process.

Prometheus makes a significant action by apprehending Green Arrow and compelling him to confess his pleasure in taking lives. Having successfully executed this plan, the antagonist allows his foe to go free and initiates the next phase of his scheme, which requires everyone to travel to Lian Yu. Despite losing their last battle, Chase takes his own life to detonate a bomb on the island, ensuring that Oliver will forever remember him.

Arrow is streaming now on Netflix.

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2025-07-17 17:42