Not even a little.
Dean Winchester and the archangel Lucifer are primarily mortal enemies who try to kill each other every chance they get though on a few very rare occasions they have been forced to become reluctant allies for a period of time.
As part of the plan for the Apocalypse, Dean was destined to be the vessel of the archangel Michael while Sam was meant to be Lucifer's vessel. In these two bodies, the two archangels were supposed to fight to the death, a fight that would destroy half the planet if Michael won. According to Gabriel, this was because Michael and Lucifer mirrored Dean and Sam.
On a personal level, Dean and Lucifer tend to be mortal enemies who often fight each other with Dean attempting to stop Lucifer's plans. Despite their status as mortal enemies, Dean has shown an ability to work with Lucifer when necessary, albeit reluctantly. In Alpha and Omega, Dean went so far as to check on the archangel after he was defeated following their failed attack on the Darkness. In Exodus, Dean was willing to work with Lucifer to repair a bus and then let Lucifer drive it, although the driving was so that he would know where Lucifer was and Castiel could keep an eye on him. During their interactions, Dean has shown no fear when faced with Lucifer in contrast to Sam at times. In The Devil in the Details, when asked by Lucifer if he was scared, Dean stated that he was "not even a little" though he was taken aback at Lucifer's antics before the fight. Dean is often defiant in the face of Lucifer, even when Lucifer has the upper hand in a situation and is always trying to figure out a way to lock Lucifer back up or kill him.
For Lucifer, he seems to regard Dean merely as an annoyance, though one he was willing to put up with and keep around during the Apocalypse to keep Sam happy. Following his return, Lucifer was interested in Dean due to his connection to the Darkness which he saw as something that he could exploit for his own benefit. After the Darkness left the Earth and Lucifer gained a permanent vessel in Nick thanks to Crowley's efforts, Lucifer lost all interest in Dean beyond getting rid of a constant annoyance to him, one that he never took seriously as a threat.
During Are You There, God? It's Me, Dean Winchester, Dean learns from Castiel about Lucifer being freed if the 66 Seals were to be broken. Dean had previously thought him to be a fairytale but was surprised to learn that Lucifer was real. After learning that Lilith is breaking the 66 Seals to free Lucifer from Hell, Dean dedicates himself to preventing his rise.
In Lucifer Rising, the angels claim that Dean will ultimately be the one to stop Lucifer, but he eventually learns from Zachariah that they want to let Lucifer rise so that they can beat him and have paradise on Earth. Dean later attempts to stop Sam from killing Lilith and releasing Lucifer with Castiel's help, but ultimately fails due to the intervention of Ruby. Dean then witnesses the devil being released from his cage.
During Sympathy for the Devil, Dean and Sam are saved from Lucifer by a mysterious force (later revealed to be God) by being placed on a plane and seeing the aftermath of the Archangel's release. With Lucifer on the loose, Dean dedicated himself to finding a way to kill the archangel. After learning of the Michael Sword, Dean believed that if he could find and use it, he could kill Lucifer only to learn that he was the Michael Sword: the one true vessel of the archangel Michael who would have to possess Dean to have his final battle with Lucifer. Dean subsequently spent months fending off efforts by the angels to get him to say "yes" to Michael so that Michael could use Dean's body to kill Lucifer, a fight which would destroy half the planet.
In The End, Dean met Lucifer for the first time when Zachariah transported him to an alternate future in the year 2014. Beforehand, Dean learned his brother was Lucifer's true vessel and understood this meant Michael and Lucifer would fight in their bodies. In the alternate world, This Lucifer possessed Sam which horrified Dean as Lucifer was shocked to see him but casually greeted him. He chose to spare Dean, right after killing Dean's future counterpart. Lucifer attempted to get Dean to understand him, but Dean bit back saying that he was like every other monster Dean hunted, the only difference being the size of his ego. Breaking into tears at failing his brother, Dean told Lucifer to kill him or he'll find a way to kill him as the latter remarked he liked Dean and ended their conversation with assuring Dean that they would "always end up here". Lucifer declared that he won before bidding Dean farewell. This trip also caused Dean to make amends with his brother and they started hunting together again.
Returning to the present, Dean sought to kill Lucifer by using the Colt. Dean attempted to do just that in a confrontation though the plan failed and Lucifer physically attacked Dean in retaliation. Dean and Sam were saved by Castiel though Lucifer wasn't fazed.
They briefly meet again in Hammer of the Gods, when Lucifer arrives at the motel Dean and Sam are trapped in by the pagan gods, who Lucifer proceeds to slaughter. However, Gabriel prevented Lucifer from claiming the brothers by fighting him off. Through Gabriel's sacrifice, Dean had learned of a way to put Lucifer back in his cage.
In Swan Song, Dean was left with relying on Sam's own plan of saying "yes" to Lucifer in order to send Lucifer back to his Cage. Dean watched as Lucifer abandoned his previous vessel for Sam, and then took Sam for his own. After gloating briefly to Dean, Lucifer departed without bothering to kill him while Dean was left horrified at this.
At Stull Cemetery, Dean interrupted Lucifer's battle with Michael and glared at him after he insulted him before stating he wanted to speak with Sam. After Castiel sent Michael away, Lucifer killed Castiel and Bobby as he proceeded to beat Dean up, calling him "a pain in my ass." Dean called out to Sam as he was attacked and Sam eventually managed to take control of his body, and return Lucifer to his prison at the sacrifice of himself. Shortly afterwards, Castiel was resurrected by God and he was able to heal Dean's injuries and bring Bobby back.
Dean did not meet Lucifer again until about five years later, when Sam convinced him to allow him to speak to Lucifer. Unfortunately, Lucifer had set up a plan to escape the Cage, and despite Dean's efforts to stop him, Lucifer got out. Dean would not known of this for a time, and conversed with Castiel, unaware that Lucifer was possessing said friend. When Dean did find out, he made an effort to rescue Castiel.
Lucifer repeatedly mocked Dean over his concern for Castiel. Originally, he planned on using Dean's connection to Amara for good use, but after discovering, and subsequently obtaining a Hand of God thanks to the brothers, he ultimately chose to be rid of Dean and Sam. His effort to kill the brothers failed when Amara herself kidnapped him, an incident which he blamed the brothers for. Later on, Dean arranged a rescue mission to retrieve Lucifer, believing him to be a necessity in the war against Amara.
Once the archangel was at the Bunker, however, Lucifer began throwing a teenage tantrum at his father, forcing Dean (and Sam) to get the two to sit down and talk. Afterwards, Dean and Lucifer worked together to fight Amara, though they continued to annoy each other. Amara eventually expelled Lucifer from Castiel's vessel, much to Dean's delight, as it returned Castiel to him. However, Dean was shown to still worry about Lucifer enough to check on him when he thought Lucifer was still inside Castiel, and asked what happened to him after his eviction.
After God and Amara's reconciliation and departure, as well as after the confrontation with Toni Bevell, Dean learned from Castiel that Lucifer was still out and about and Castiel planned to capture him, something Dean offered to help with. Eventually, Castiel accepted his help and Dean traveled to Los Angeles to interrupt a concert Lucifer was hosting. Dean succeeded in chasing the guests out with gun shots fired at the ceiling. Lucifer was obviously unhappy about this, and he and Dean, Sam and Castiel got into a brief struggle, in which Dean handcuffed Lucifer.
Lucifer greeted him with mild surprise and threw him off the stage and melted the handcuffs from his wrist. Dean then bore witness to Lucifer's confession and why he was motivated to kill people randomly. Dean showed no remorse over Lucifer's sense of betrayal caused by his father's abandonment, and merely looked on in dislike as Lucifer vowed to destroy the humans in retaliation. Dean taunted Lucifer about the deterioration of his vessel, to which Lucifer agreed that Vince Vincente was wearing thin, and promptly left the vessel. Dean vowed to capture him.
Dean and Sam followed Lucifer to a church and then towards the President of the United States, who was Lucifer's next choice for a vessel. When Castiel sensed the conception of Lucifer's child, Dean remarked how he didn't know the archangel was dating. Dean later accepted help from Arthur Ketch and used his equipment to free the President from possession and send Lucifer back to Hell. Both and Sam expressed joy at finally defeating Lucifer.
Months later, Dean finds out that Lucifer had not been returned to the Cage due to Crowley's personal intervention, which has allowed Lucifer to escape a much weaker confinement. Dean angrily confronts Crowley about this, but agrees to work with Crowley again in defeating Lucifer, who is now in search of his unborn son. Dean, Sam and Castiel confront Lucifer outside Kelly's cabin, and plan to lure him and trap him inside a portal opened up by Lucifer's son. Once Lucifer is inside, Dean acts as a distraction by firing numerous bullets into Lucifer while Sam and Crowley finish the spell to close the portal.
Lucifer is unharmed, and while the spell gets completed, Lucifer is still able to escape the portal and kill Castiel right before Dean's eyes. Dean then witnesses his mother and Lucifer fall back into the portal during a scuffle between the two. The portal closes behind them, leaving Dean with a dead Castiel.
Dean is quick to convince himself that Lucifer has murdered his mother and initially treats Jack with disdain since he is Lucifer's son.
During War of the Worlds and The Bad Place, he assists both Sam and the resurrected Castiel in convincing Jack to choose them over his father which they succeed. He also learns from Jack that Lucifer has not killed Mary though unaware that Lucifer himself has returned.
In Devil's Bargain, Dean was shocked to hear from Castiel that an alternate Kevin used a spell that allowed Lucifer to return. When confronting Lucifer, Dean was angry to see him again and made it clear that he will kill the latter in time but needed to get Jack and Mary away from the alternate Michael who wants to invade their world. However, Anael aided Lucifer who began torturing Dean, Sam and Castiel but Arthur Ketch intervened and Lucifer retreated.
The two met again in Beat the Devil, after Gabriel and Rowena MacLeod captured him and brought him back. Dean was pleased to see him in a weak state and nodded in agreement with Sam to killing Lucifer after rescuing their mother. Lucifer didn't protest this but when learning from Rowena that Jack is in Apocalypse World, he broke free and got sent to the world by the witch once he attempted to kill her. Dean became shocked when Sam (who was killed by vampires) returns to his family and is followed by Lucifer who resurrected him.
During Exodus, Dean was angry to see Lucifer again even more so as the latter approached Jack. He was determined to make sure they stayed separated by telling Gabriel to kill him as Lucifer remarked that he resurrected Sam and the family needed him against Michael. Reluctantly, Dean allowed Lucifer to join the group but was worried about his influence on Jack and they worked in evacuating the apocalypse world survivors to Earth. Dean also watched in horror as Lucifer was defeated by the alternate Michael. Dean referred to Lucifer being trapped as "Sam handling it", unaware that Lucifer was making a deal with Michael to cross over.
In Let the Good Times Roll, Dean is shocked when Lucifer arrives in the Main Universe with Michael. During the confrontation between Lucifer and Jack, Dean helps to expose Lucifer's deal with Michael and his murder of Maggie which causes Jack to turn on Lucifer. To Dean's horror, Lucifer steals Jack's grace and disappears with Jack and Sam.
Following Lucifer's departure, Dean learns from Michael that Lucifer is now super-charged from stealing Jack's grace and can destroy the whole universe if he wants to. With Michael too weak to defeat Lucifer in his current state and desperate to save his brother and all of Creation, Dean remembers that he is the Michael Sword, Michael's one true vessel with whom he will be stronger than ever and offer Michael a deal to finally defeat Lucifer. Despite Castiel's protests, Dean sees no other choice but to become Michael's vessel due to threat Lucifer poses. Dean and Michael are able to reach an agreement where Dean says "yes," but Michael allows Dean to remain in control while Michael powers him from within.
|“|| You let my brother in.|
Well it turns out we have something in common: we both wanna gut your ass.
Dean arrives in time to prevent Jack from committing suicide to save Sam and faces Lucifer in battle. Powered by Michael, Dean is able to put up a far better fight against Lucifer than he has in the past, but still proves to be no match for the super-charged archangel. As Lucifer tries and fails to smite Dean, Sam tosses Dean Michael's archangel blade, allowing Dean to finally kill Lucifer with it.
|“|| He... He's dead.|
You did it.
No. No, we did it.
Despite being the one to kill Lucifer, Dean is shown to hardly be able to believe it in the aftermath of their fight. Though Sam gives him credit for it, Dean shares credit with his brother. However, Dean's desperate deal to defeat Lucifer results in Michael taking full control of his true vessel and being let loose upon the Main Universe.
In the alternate reality seen in The End, Dean leads a resistance movement against Lucifer who has taken Sam as a vessel. Dean leads a final suicidal mission to kill Lucifer with the Colt, but he fails and his neck is snapped by Lucifer in front of his present-day self. During his conversation with the Main Universe Dean, this Lucifer is amused by his threats, but admits to genuinely liking Dean and understanding the angels interest in him, going so far as to try to get Dean to see his point of view.
- During his first meeting with Lucifer in The End, Dean threatened that if Lucifer didn't kill him immediately, he would find a way to kill him some day, a threat that Lucifer didn't take seriously. In Let the Good Times Roll, Dean made good on this threat when he finally killed Lucifer with an archangel blade.
- Its unclear if the alternate Dean actually managed to shoot Lucifer with the Colt or not in The End. Given Lucifer's immunity to the Colt's power, he would've survived even if he had been shot and thus still would've been able to meet with the Main Universe Dean after the alternate Dean's death.
- Dean has made two direct attempts to kill Lucifer.
- Dean shot Lucifer through the head with with the Colt in Abandon All Hope.... However, Lucifer was one of five things the gun couldn't kill and it didn't work.
- In Let the Good Times Roll, Dean attempted to kill Lucifer with an archangel blade while powered by the alternate Michael whom Dean was acting as a vessel to. In this instance, Dean succeeded in killing Lucifer.
- In O Brother, Where Art Thou?, Dean calls Lucifer "the biggest monster ever hatched" despite all of the other threats that the Winchesters have faced up until that point. In return, Sam considers Lucifer second to Amara following her recent release.
- During most of the Winchesters conflicts with Lucifer, it is most often Dean who attempts to engage him in combat.
- Dean and Lucifer have fought hand-to-hand twice: once in The Devil in the Details in a cage in Limbo and once in an abandoned church in Let the Good Times Roll.
- In the first instance, Dean fought alongside Sam and Castiel and was no match for Lucifer who taunted Dean that "you hit like a human" with Dean's blows not bothering Lucifer at all.
- In the second instance, Dean was powered by an archangel and equipped with the strength of one as a result, but was no match for the super-charged Lucifer. However, he ultimately won the fight and killed him.
- Dean has shot Lucifer twice.
- In Abandon All Hope..., Dean shot Lucifer in the head with the Colt at point-blank range. Lucifer survived as he was one of five things that the Colt can't kill.
- In All Along the Watchtower, Dean shot Lucifer with a hundred angel-killing bullets from Rufus. While sufficient to distract Lucifer briefly, the bullets couldn't kill him either as he was an archangel and immune to them.