Arrow's Oliver Queen (Stephen Amell) and The Flash's Barry Allen (Grant Gustin) may be good friends, but they've still had their share of violent fights in the Arrowverse. The relationship between Barry and Oliver goes all the way back to Barry's introduction in Arrow season 2. The pair, who are the protagonists of the first two Arrowverse shows, have teamed up in six annual crossover events.
Outside of the Arrowverse specials, the two have also made occasional guest appearances in each other shows, such as the time Oliver showed up in Central City to help Barry defeat Reverse-Flash (Tom Cavanagh), and the incident where Barry traveled to Nanda Parbat to save Team Arrow when they were captured by Ra's al Ghul (Matt Noble). Barry and Oliver's friendship isn't just an important part of the crossovers; it's also important to their characters' individual stories in the Arrowverse well. Barry was even part of the reason why Oliver agreed to help the Monitor (LaMonica Garrett), and Oliver's heroism was a major influence on Barry's life.
Their story came to a tragic conclusion when Oliver - as the Spectre - died in the final battle with the Anti-Monitor in the fourth installment of the 2019-2020 Arrowverse event, Crisis on Infinite Earths. Oliver received a chance to spend his final moments talking to two of the most important people in his life, Sara Lance (Caity Lotz), and of course, Barry Allen. However, not all of Oliver and Barry' s scenes in the Arrowverse have been touching moments. The two have even fought on a few occasions. Here's every time Green Arrow fought the Flash in the Arrowverse, and who won each time.
In the first-ever Arrowverse crossover, a two-part event called "Flash vs. Arrow", Oliver and Team Arrow visit Star City and meet Barry's friends for the first time. Oliver is on a mission to take down an enemy of his own (Captain Boomerang), but ends up getting entangled in Team Flash's problems, as they're currently dealing with a metahuman called Prism. Barry is naturally excited about working with Team Arrow, but Oliver is intent on making sure Barry takes things more seriously. He takes it upon himself to train Barry, especially since Barry has no actual experience when it comes to fighting. Oliver asks Barry to attack him, and explains that he'll retaliate with an arrow.
What follows can barely be classified as a fight, because Oliver wins it before it even starts. Barry catches Oliver's arrow, but fails to notice the arrow trap Oliver has rigged up behind him. Barry is blindsided by arrows that him in the back. Oliver wins this encounter, and it served as a lesson for Barry, who still had a lot to learn about tactical awareness.
In the same episode, "Flash vs. Arrow", Prism uses his metahuman powers on Barry, which sends him into a fit of anger. Barry is out of control, forcing Oliver to stop him. Oliver takes advantage of Barry's lack of training and fires an explosive arrow near Barry, who thinks that Oliver simply missed. The ensuing explosion knocks Barry back, and Oliver follows up with a tranquilizer arrow. Barry seems to shrug it off and keeps fighting. Oliver, nearly overwhelmed by Barry's amazing speed, has no choice but to go on the defensive. Oliver struggles to land a blow on Barry, who moves so fast that Oliver can't keep up with him.
Even so, Oliver does manage one hit. Oliver uses his super speed to pummel Oliver with several consecutive punches, and just when it appears that Barry is victorious, Oliver activates another trap. Barry is ready this time, but as it turns out, it was only a distraction. Oliver flings an arrow into Barry's leg, wounding him. It may have been another tranquilizer arrow, because he was slow enough for Oliver to catch Barry's fist and trap him in a headlock. Team Flash arrives and is able to use a device to return Barry back to normal. Both Oliver and Cisco (Carlos Valdez) have accepted this as a tie, though it did look as if the victory went to Oliver, considering that he had Barry immobilized.
At the end of the second part of the "Flash vs. Arrow" crossover, Oliver takes Barry to an empty warehouse where they can settle once and for all which one of them would win in a fight. No one is around to watch, since Oliver decides that he would rather this be something that only they need to know. Once again, Barry fails to take Oliver seriously as an opponent. This becomes apparent when he points out that Oliver has "arrows that run out," while he, on the other hand, has real super powers. Regardless, Oliver is determined that they battle it out. Barry agrees, and the episode ends with Oliver firing arrows at Barry and Barry charging toward him. The episode leaves the question of who won open to interpretation.
This scene is clearly meant to pay homage to Rocky III, which wrapped up with Rocky (Sylvester Stallone) having a private match with Apollo Creed (Carl Weathers). Similar to Rocky III, "Flash vs. Arrow" leaves the outcome of the fight a mystery. Even so, it does get brought up again in the Legends of Tomorrow episode of the "Invasion!" event. At a bar, Barry mentions that it was he who won the fight. This is confirmed when Oliver doesn't dispute Barry's remark, and only points out that there were no witnesses.
In the "Elseworlds" crossover, reality is tampered with, causing Barry Allen to become Green Arrow and Oliver Queen to become the Flash. After a trip to Gotham City, the body-swapped heroes are infected by Scarecrow's fear gas. The result is that Oliver sees Barry as Reverse-Flash (Tom Cavanagh) and Barry sees Oliver as Malcolm Merlyn (John Barrowman). The two become engaged in a heated, evenly-matched fight with each character getting in plenty of hits. Before anyone can win, the two are interrupted by the arrival Batwoman (Ruby Rose). No winner was ever determined, but seeing which is of them was superior wasn't the point this time. This fight allowed both characters to develop a better understanding of both each other and what they've gone through by having them come face-to-face with two of their biggest villains.
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