When one thinks of the most powerful and skilled heroes in DC Comics, Green Arrow isn't usually one of the first to come to mind. However, he is one of the most talented and creative fighters in the DC Universe, able to come up with unconventional solutions to unconventional problems. He can also brawl with the best of them, and his trick arrows can easily turn the tables in a battle.

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However, there are several enemies that even Green Arrow hasn't been able to conquer, and even more that weirdly haven't really crossed his path despite the circles he travels in.

10 Green Arrow Was Tasked With Catching Catwoman Once, And She Got Away

Catwoman Stealing

For a time, Green Arrow and Catwoman were both a part of a government-run Justice League of America team, but Catwoman seemingly turned on the rest of the group to accomplish a task for a mysterious benefactor. Green Arrow was among the first to try and subdue Catwoman, but she got away.

Ollie and Selena haven't traded blows since then, and it's unclear if Green Arrow could win this showdown--or if the Catwoman's tricks would leave the Emerald Archer stumbling.

9 Green Arrow Hasn't Tested His Skills Against Nightwing

Nightwing Bludhaven 2

Despite some of the barbs--both verbal and physical--traded between Green Arrow and Batman over the years, Ollie has never had much trouble with Batman's first son, Nightwing aka Dick Grayson.

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Both have been members of the Outsiders team in the past, but this hasn't led to either testing their skills against the other. Nightwing's fighting skill and agility are legendary, so it's hard to imagine Ollie would do too well in this matchup.

8 Green Arrow Has Never Matched Arrows With The Huntress

Huntress Infinite Frontier 1

Helena Bertinelli (or Helena Wayne on Earth-2) is known for making use of a crossbow during her missions and while working as part of the Birds of Prey team. She was also at odds with Green Arrow in CW's Arrow television series.

However, the two have never really fought in the comics despite some disparate views on how to handle crime. It's not really known which archer would win the day if they ever did fight.

7 Black Canary And Green Arrow Have Sparred, Usually With Black Canary Winning

Black Canary using her Canary Cry

Green Arrow and Black Canary have been both romantic partners and crimefighting partners several times over the years. The two were even married for a time, and they still seem to be involved right now despite that marriage falling apart (it was pre-Flashpoint DC.)

Ollie and Dinah have sparred several times over the years, though it has come to genuine blows before. In almost every case, Black Canary won. If she didn't, then there was no clear victor or one of the two had to beat a retreat.

6 Lex Luthor Has Never Been Brought Down By Fellow Billionaire Green Arrow

Lex Luthor in armor.

Green Arrow and Lex Luthor run in some of the same circles thanks to each man's exorbitant wealth. Green Arrow has taken on Luthor on a few occasions but to no real consequence.

Green Arrow takes a more direct approach to his problems than Luthor, and Luthor is able to keep a step ahead of Oliver Queen. Unfortunately for Green Arrow, he's never been able to do much about the Luthor problem.

5 Green Arrow Has Never Met And Fought The Joker

Joker in straight jacket

Weirdly enough, Green Arrow has never fought the Joker. Ollie isn't really known for spending time in Gotham City, and the Clown Prince really only has eyes for Batman and his closest associates. That said, the Joker has still been a part of the Secret Society and the Injustice League before, and he's been known to hassle the likes of Superman on admittedly rare occasions.

The Joker seems like the kind of problem Green Arrow would decide to deal with personally, even if it infuriated Batman. A showdown between the Emerald Archer and the Clown Prince of Crime would certainly make for a compelling story.

4 Deadshot And Green Arrow Have Met, But Neither Marksman Won The Day

Deadshot shooting

There was a time during the Deadshot miniseries by Christos Gage and Steven Cummings in the mid-2000s that found Floyd Lawton taking up residence in a particularly seedy part of Star City to watch over his estranged daughter. Naturally, Deadshot's antics eventually caught the attention of Green Arrow.

Ollie was planning on taking the assassin in and seemed to be getting the better of Deadshot...until the people of this neighborhood came to Deadshot's aid. It turns out Green Arrow hadn't patrolled this neighborhood very often, and poverty and crime had really taken its toll on the people who lived there. They liked having their own guardian, and this led to Ollie and Floyd talking it out instead of shooting one another.

3 Green Arrow And Hawkman Really Don't Like Each Other

Hawkman From DC

Green Arrow and Hawkman are at ideological odds. Green Arrow is on the left, while Hawkman is implied to be a bit more on the conservative side (though this is almost never really dug into much.) During the "Slings and Arrows" arc of Geoff Johns and Rags Morales' run on Hawkman, Ollie and Carter had it out with no real victor.

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The two would collide again during the Hawkman: Wanted crossover in Savage Hawkman, Green Arrow, and Deathstroke titles in the New 52, but they ended up working together to help protect Hawkman from his Thanagarian pursuers.

2 Green Arrow And Batman Have Been At Odds Several Times--Usually With Batman As Victor

Batman Peacekeeper

Green Arrow and Batman are really not fond of one another. The Dark Knight thinks Ollie is too much of a brash loudmouth, and the Emerald Archer thinks that Bruce is pompous, cruel, and arrogant.  They've had their fair share of shouting matches while part of the Justice League.

Upon occasion, this does lead to an outright brawl between the two, and Batman always wins.

1 Green Arrow Just Can't Seem To Beat Deathstroke The Terminator

Deathstroke fighting

Despite Deathstroke being nominally part of the Teen Titans rogues gallery but still hassling Batman on the regular, Green Arrow and Slade Wilson have fought each other several times over the years--especially in 2000s DC Comics.

There is the famous Identity Crisis fight that finds Green Arrow plunging a broadhead into Slade's bad eye, which prompts Slade to beat the tar out of Ollie until the entire Justice League manages to physically restrain Slade. They had another duel during Judd Winnick and Phil Hester's "Road to Jericho" arc in Green Arrow. They've fought a few times since then too, but Ollie just cannot seem to get the better of Slade.

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