Oliver Queen / Green Arrow

Earth-One / Post-Crisis / New Earth

 * 1)  Bonnie King  was an early love interest of Oliver's. When all the Justice League members took their respective love interests to a carnival, she accompanied him (Justice League of America #7, Nov. 1961).(Justice League #7)
 * 2)  Dinah Lance / Black Canary  - The two became an item after she joined the Justice League, and were somewhat off-and-on for years.
 * 3)  Joanna Pierce  was a lawyer (and the nephew of Jefferson Pierce, AKA Black Lightning) who befriended Oliver. This apparently included some form of romance, but this relationship ended in her death, something that drove a wedge between Oliver and Jefferson.

Oliver and Dinah eventually committed to each other and were married.

New 52

 * 1)  Dinah Lance /Black Canary  - Oliver has a history of romance with Dinah in this version as well.

Kingdom Come

 * 1)  Dinah Lance / Black Canary  and Oliver are married with a daughter, the new Black Canary.

DC Animated Universe

 * 1)  Dinah Lance /Black Canary  - Oliver initially wants to leave theJustice League after one mission, but changes his mind when he sees Black Canary. After one adventure together, the two become an item.

Smallville
In Smallville, Oliver and Dinah fight alongside each other, but never fall in love.
 * 1)  Lois Lane  - When Oliver first moves to Metropolis and begins acting as a vigilante, it is reporter Lois Lane who gives him the name “Green Arrow Bandit,” which others shorten to “Green Arrow,” much to her chagrin. As Oliver Queen, he and Lois begin a relationship, which is complicated by his secretive lifestyle, ending in their breaking up. Later, she learns his identity as the Green Arrow and, with this out in the open, he discusses renewing their relationship. She states that she cannot be a superhero’s girlfriend, although she later breaks this rule to be with Clark. Oliver remains close to Lois and Clark, even serving as best man at their first attempt at a wedding. This wedding ends in disaster when Oliver, possessed by Darkseid, breaks into a fight with Clark.

When Oliver finds out that Chloe has been monitoring communication between league members, he pleads “Those e-mails between Canary and I were entirely platonic!” both referencing his relationship with Canary in the comics and hinting at his desire to be with Chloe.
 * 1)  Chloe Sullivan  - Oliver grows close to Chloe, who serves as the behind the-scenes tech agent, of the team of superheroes.

The two eventually begin having casual sex. When Oliver believes he will die in the field, both he and Chloe confess their love for each other. Afterward, they begin a relationship.. The entire superhero team is later afflicted with a sort of science-fiction inebriation, causing them all to do crazy things and not remember them. Chloe and Oliver realize that they, in this time, got married. However, they decide to not annul it, but remain a married couple. Years later, they have a son.

Arrowverse
The first time was with a girl named Samantha, whom he got pregnant. Samantha, bribed by Oliver's mother to disappear, then told him she miscarried and left town to raise their son on her own. Oliver then cheated on Laurel with her sister Sara. Later, it was discovered that Sara was still alive, and now on the island. The villainous Anthony Ivo put her and Shado at gunpoint, telling Oliver to choose between them. Oliver threw himself in front of Sara, and Ivo shot Shado in the head, killing her. Later, after defeating Ivo and fighting an insane Slade, Sara went into the sea again, once again presumed dead. Oliver had many more adventures before returning home. It was once insinuated that he had feelings for Taiana, a Russian girl who had also been kidnapped and taken to the island. This was complicated by the fact that Oliver had killed her brother in a fight. When she became possessed by an evil spirit, she begged Oliver to kill her, and he did so by breaking her neck.
 * 1)  Laurel Lance . Black Canary - Oliver Queen grew up a spoiled rich kid, although he maintained a close relationship with the Lance sisters, Dinah, who in this version goes by her middle name Laurel, and Sara, who came from a middle class family. In college, Oliver dated Laurel, but cheated on her at least twice.
 * 1)  Sara Lance   and Oliver were on a trist together on his father’s boat when it sank and he was marooned on the island Lian Yu, believing her to be dead.
 * 2)  Shado  - Oliver met many people on the island, including Shado, a young Chinese woman and deadly martial arts expert who had been kidnapped and taken there. After defeating her captors, Oliver lived on the island with Shado and Slade Wilson for months. Slade developed feelings for Shado, but she and Oliver became a couple.

When Oliver briefly returned home without any of his friends and family knowing, he was in the Queen Industries building, where he caught his first glimpse of employee Felicity Smoak, who would later occupy his life greatly. After returning home, Oliver reconnected with Laurel, and they agreed to try to be friends. 4.  Helena Bertinelli / Huntress  - Now a vigilante, Oliver was investigating crime boss Frank Bertinelli, and came into contact with his daughter, Helena. Helena and Oliver connected, went on a date, and had sex. He later discovered her to be the vigilante known as Huntress, out for vengeance against her father for killing her fiance. Although Oliver himself used lethal force at this point, he disapproved of her more ruthless methods, and the two came to blows before she fled.

5.  McKenna Hall  - Oliver then started dating a friend of his, a police officer. A jealous and psychotic Helena came back into town and attempted to harm McKenna before being fought off. After this, an injured McKenna left Starling City, and Oliver.

5.  Felicity Smoak  - Oliver recruited tech genius Felicity Smoak into his crusade at an early stage. It was soon suggested that she had feelings for him. Although at the time these seemed one-sided, it would later become clear that Oliver at least had a fascination with Felicity from their first meeting, even remembering the color of pen she was chewing (red).

Laurel had begun dating Oliver’s best friend Tommy Merlyn, but Tommy eventually broke it off, believing she was still in love with Oliver, and telling both they should be together.

Laurel and Oliver renewed their relationship. After Tommy’s death soon after, a distraught Oliver left Starling City and Laurel, returning to Lian Yu.

When Oliver returned to Starling City months later, he and Laurel again agreed to be friends.

Sara then turned up, revealed yet again to be alive, and joined Oliver as a vigilante known as The Canary. He and Sara renewed their own relationship, at first to Laurel’s chagrin, but later with her blessing. Sara eventually broke up with Oliver because she felt her dark personality was bad for him.

Oliver then connected with, and had sex with, the CEO of his company, Isabella Roschenko, but she turned out to be an evil agent of Slade Wilson’s, out to destroy him.

When Oliver's now-enemy Slade Wilson kidnapped Laurel, believing Oliver to be in love with her, Oliver, knowing he was being recorded by Slade, told Felicity that she was the one he was truly in love with. This was a ploy to get Slade to attempt to kidnap Felicity, to make him fall into a trap. However, Oliver's friend John Diggle then insinuated that Oliver really did love Felicity, and encouraged him to act on his feelings.

Oliver admitted his feelings for Felicity and asked her out on a date. That date ended with an enemy of his sending a missile into the restaurant, almost killing them both. Oliver decided a relationship with Felicity is too dangerous for her, but admitted that he loved her.

Later, to save his sister’s life, Oliver agrees to become Ra’s Al Ghul’s student and successor for the League of Assassins. Before he bids farewell to Felicity, the two have sex. After turning on and defeating Ra’s Al Ghul, he decides to retire from vigilante life and live with Felicity.

Oliver and Felicity decide to return to vigilante life months later. He also discovers he has a son with Samantha Clayton. Samantha tells him that she will not allow him visits if he tells anyone else about the boy, William, so he keeps it a secret from Felicity. Soon after, the two become engaged.

Laurel, who had sinced joined Oliver’s crusade as The Black Canary, was killed by Damian Dahrk. Before she died, she told Oliver that although she wasn't the love of his life, he would always be the love of hers.

When Felicity learns about Oliver keeping his son a secret, she breaks up with Oliver, stating that his way of keeping secrets has become too intrinsic to him, and later stating that she cannot stand that he doesn't trust her.

Later, when Oliver is placed in an alien machine to make him live out an ideal reality, he finds himself engaged to Laurel.

6.  Susan Williams  - After becoming mayor, Oliver started dating reporter Susan Williams, who was also investigating his ties with the Russian mafia in his past. Oliver’s sister Thea faked evidence that Susan reported a false story, getting her fired. Not believing that Oliver had nothing to do with it, she broke up with him. The villain Prometheus eventually revealed to her that Oliver is the Green Arrow. Oliver set everything straight with her, and got her her job back, but did not believe they should renew their relationship.

After simmering tension remained between him and Felicity, the two ultimately got back together. They later decide to very quickly get married. After Samantha Clayton was killed, Oliver and Felicity took in Oliver's son William, but after some time, it was decided by all, including William, that it was best for him to move in with his maternal grandparents.

Oliver made a deal with a cosmic, near-omnipotent being named Mar Novu to help him, when his services would be needed, to overcome a great enemy. In time, Oliver and Felicity once again retired from superhero life, and they have a daughter, Mia. This idyllic life is cut short when Oliver's services are called upon by Mar Novu. Novu also informs him that he has seen the future and knows Oliver's death to be imminent.

Oliver goes on a mission to help Novu for months, separating him from his family, in order to defeat the enym, Mobius, the Ant-Monitor. Finally, in the first battle of the conflict known as the Crisis on Infinite Earths, Oliver was killed by an army of the Anti-Monitor's shadow demons.

Oliver's friends attempted to bring him back to life, but his soul was taken on yet another mission by the mystical being known Jim Corrigan, the Spectre, who would turn Oliver into his own successor as the near-omnipotent Spectre. After the Ant-Monitor succeeded in not only killing Mar Novu but destroying the Multiverse, Oliver took a group of heroes to the dawn of time to reset the universe and change the series of events leading to its destructino. He then died again fighting the Anti-Monitor, yet in the struggle succeeded in his mission.

This new, "Post-Crisis" reality differed in many ways. Oliver reset the timeline to be more ideal for himself, including saving several of his deceased loved ones from their fates. In this timeline, neither Tommy Merlyn or Laurel Lance had died, and the two had gone on to be married.

In an alternate future, one which was ultimately changed by Oliver's time-travelling children, and apparently one in which Mar Novu survived, Felicity was taken by Novu into the afterlife in which Oliver's soul existed, reuniting the two forever.

Additionally, on Earth-X, Oliver’s doppleganger was the leader of the world Nazi government, and married to Overgirl, the doppleganger of Kara/Supergirl. This version was killed by Oliver himself.