Batman is has one most intelligent characters within the DC universe. He seems to outsmart pretty much everyone, including some of the biggest bads in the universe that have ancient knowledge. The World's Greatest Detective is said to even be more intelligent than those who have seemingly unforeseen knowledge and pretty much always manages to come out on top.
Yet, there still remains incidents in which Batman was outsmarted and bested by some of his greatest enemies and his closest allies. Each time Batman is outsmarted seems like a big deal to the fans, as it is not a frequent occurrence.
10 Alfred Pennyworth
Alfred Pennyworth has outsmarted Bruce Wayne a number of times throughout his life, in a number of different ways. However, there is one instance that truly sticks out. In the esteemed story by legendary author, Neil Gaiman, Whatever Happened to the Caped Crusader?, Batman is outsmarted for a number of years by Alfred. After suffering from more than a few mental breakdowns to his failure of catching villains, Alfred gets a few members of his old theater troupe to pretend to be some of the notorious villains, donning the Joker outfit himself. This works for years, as Batman thinks he is fighting and apprehending real criminals, but really they are all just actors in costumes.
9 Talia Al Ghul
Talia outsmarted Batman on a few occasions, but one of the most notable happens to be the conceiving of Damian Wayne. Talia may have drugged Bruce to create Damian. This is debated widely & argued among fans as many comics have implied that it was consensual (and depicted as such in Son of the Demon,) while most imply that Talia had drugged Bruce. Either way, Talia got what she wanted: Bruce's son. And she outsmarted him a number of times in the exchange, including the fact that she hid Damian for years before he found his father again.
8 Tim Drake
Tim Drake is the third Robin, and arguably the best detective in Gotham. Tim has a photographic memory and skills when it comes to being an amazing sleuth. Bruce even regarded Tim as a better detective than himself.
Tim was able to figure out that the first Robin was Dick Grayson by recognizing some of his moves from when he saw the Flying Graysons in the circus as a child. Because he knew that Bruce Wayne was Dick's adopted father, he also uncovered Batman's secret identity.
7 Bane
Bane has outsmarted the Bat a number of times throughout the comics, showing time and time again that he has brains & brawns. Bane is probably one of the smartest Batman villains and can best him in mind and body. One of the most notorious instances was during the iconic Knightfall when Bane broke Batman's back. The events of Knightfall occur shortly after A Death in the Family when Jason Todd is brutally murdered by The Joker, making Batman be a bit rough around the edges. Bane released a number of high-threat villains from Arkham, and Batman finds himself getting more and more tired and weak with each one he faces. After putting a large number of them away, he is then confronted by Bane. But the tired Dark Knight is no match for Bane, and he is immediately bested and broken.
6 The Riddler
While The Riddler's entire life goal seems to be that he wants to prove that he is smarter than "The World's Greatest Detective," it seems like he may have already done so. During the events of "The War On Jokes and Riddles," The Riddler pushes Batman to want to kill. This is something The Joker has been aching to achieve, and though he could also be credited with this achievement, it was the Riddler who really set him off. Batman attempts to stab The Riddler in the face to kill him but is stopped by The Joker.
5 Hawkgirl
Hawkgirl starred in the animated Justice League and Justice League Unlimited alongside the Dark Knight. She was incredibly intelligent and a total force to be reckoned with, making her become one of the fan-favorite characters in the series, alongside being one of the only other female cast members next to Wonder Woman. Hawkgirl is seen playing chess with Batman time & time again and actually beats him almost every time. She can be seen entering the Batcave without triggering any of the alarms, meaning she outsmarted the Bat's traps.
4 Jason Todd
Like Tim Drake, Jason Todd was a Robin who exceeded Batman in one of his main traits: combat. Batman acknowledged that Jason was probably the best fighter he knew, even better than himself. he was smart and agile and knew exactly when to attack.
In Under the Red Hood, Jason disguises himself as the Red Hood, a foe that Batman doesn't recognize as his former protege. To be fair, Jason was supposed to be dead. He was brutally murdered by The Joker and then resurrected using the Lazarus Pit. He outsmarted Batman and almost makes the Great Detective second guess his own way of being, making him actually consider killing The Joker.
3 Onomatopoeia
The Widening Gyre is a pretty strange comic in which Batman was not his best self. In fact, he was pretty silly and neither at his most cautious or wisest. Onomatopoeia is a serial killer who targets heroes without superpowers. The crazed villain disguises himself as a fellow vigilante, Baphomet, who gains Batman's trust. After Batman willingly tells him who he is and shows him the Batcave, he introduces Baphomet to his new fiance, Silver St. Cloud, who immediately gets her throat slit by Onomatopoeia. The comic ends right there, so he stays one of the few to endlessly outsmart Batman.
2 Hugo Strange
Hugo Strange is another underrated Batman villain, who often comes out on top when faced against the Dark Knight. In the hit video game, Arkham City, Hugo Strange discovers Batman's secret identity just as he is the first to discover it in the comics. Strange tries to not only defeat Batman, he also tries to send Bruce Wayne to bankruptcy by convincing the Wayne Enterprise shareholders to sell him their shares in the company.
1 The Joker
The Joker is obviously Batman's most notable villain, his other half in a sense, and it should come as no surprise that there are times that the Clown Prince of Crime has actually won. In The Killing Joke, one of the most prolific Joker-based comics, The Joker finally tells a joke that gets Batman to laugh. He has been trying to succeed at this goal for his entire criminal career, and it finally happened. The two spend the rest of the pages in the comic in a fit of laughter together. It is also left to the reader's interpretation, but it is possible that the Joker did convince Batman to kill him in the final panels of the comic.