There's absolutely no question about who Norman Osborn's chief foil is...the one and only Spider-Man (Peter Parker). But Norman has never focused his anger strictly on the web-slinger, in fact Osborn's #2 antagonist is most likely Tony Stark. Interestingly though, in some ways Stark is a better match with Osborn than Peter. For starters, they're both older than Peter and they're both very wealthy industrial magnates.
The purpose of this section of the Goblin's Hideout is to document the history between the Norman Osborn and Tony Stark. The focus here is to examine their direct interactions over the years, both in and out of the Spiderverse. So without further adieu...
As you can see, there's certainly no love lost between these two Marvel heavy weights...
The earliest connection (in terms of Marvel Universe Chronology not publication date) between Osborn and Stark that I could dig up came from Marvels #2. This issue takes place around the time Professor X and his X-Men first appeared publicly. The two panels below perfectly illustrate the difference between Osborn and Stark. Osborn, although included amongst the rich elite, does not revel in their company. In fact, he looks downright miserable. Stark on the other hand relishes in the opulence and everyone seems to love him in the process. The duo (Stark and Osborn) are attending the unveiling of an Avengers statue. 
Norman is detained after an assassination attempt on an Atlantean delegate, as seen Civil War Front Line
The Green Goblin's attack on Urich is abruptly cut short after the nanites in his system take over (Stark apparently thought Norman was taking it too far), as seen in Civil War Front Line #5
After defeating the Skrull threat in Washington D.C., Norman goes on TV denouncing the use of Starktech, as seen in Thunderbolts #125
Norman watches Stark flee the front line and realizes that this is the opportunity to steal the spotlight, as seen in Thunderbolts #125 
The Ghost helps Norman to break into one of Tony Stark's vaults containing Iron Man suits, as seen in Dark Avengers #1 (top panel)
Stark shuts down Osborn's Iron Patriot armor, as seen in Siege #3
Osborn's body disintegrates after the Avengers overwhelmed his Super Adaptoid Technology, as seen in The Avengers (V4) #24
Of course, this leads to Stark Tony a bit mad...
Norman was again depicted amongst Tony Stark's social circle
in Iron Man (Vol. 3) #1. This
time he was offering Stark advice during the Heroes Reborn storyline and, as
expected, Norman was emphasizing the failure it is to be seen as weak.
Later in Iron Man (Vol. 3) #37,
Stark spots Osborn talking with Rumiko Fujikawa (aka 'Ru') and he thinks to
himself how much he hates Norman.
The interesting aspect about that revelation is that it's not clear just
where that hate began. Did Peter
Parker confide in Stark the truth about Osborn? Was it based in Osborn's reputation as a ruthless
businessman and/or was there a deal that went south between the two? Either way this marks the first
declaration of antagonism between the two men.
Keeping with the theme of
rich elite gatherings,
in a retconned story featured in Uncanny X-Men Annual #2, Osborn is once again seen amongst the world's elite at the Hellfire Club. However, this time he was not enjoying himself. After Tony Stark, while flirting with Emma Frost, inadvertently spilled his champaign on Norman causing him to flip out on Stark. Sebastian Shaw stepped in calm Norman down and when Norman flipped out on him too, Shaw snapped his finger, breaking it. Norman was then forced to leave the party.
A few years would pass
before Stark and Osborn would cross paths again, this time it would be as their
alter egos. In Marvel Knights
Spider-Man #10 Norman unleashed the Sinister Twelve on Spider-Man and the Black
Cat. The pack of villains was too
much for the two to handle luckily for them MJ had contacted the Avengers who
swooped in to take on the fight.
Iron Man and the Green Goblin did not trade blows but for a brief moment
they were in close proximity, so that counts for something!
During the course of the Superhuman Civil War the relationship between Stark and Osborn took an unpredictable turn and the result of that shift would have drastic effects on the Marvel Universe in the years to come. For a complete summary see this section because the following will not be a thorough overview.
When Peter Parker publicly unmasked as Spider-Man he took the opportunity to also throw Norman Osborn under the bus as the Green Goblin. Norman, who was in S.H.E.I.L.D. custody at the time, was none too pleased with Peter 'breaking [their] rules' so he decided to take on a new strategy...which meant working with Stark.
Tony used Osborn (as the
Green Goblin) to wreak havoc (blowing up buildings, assassination attempts,
etc) in an effort to drum up support for the Pro-Registration side. Norman was able to come and go from
S.H.I.E.L.D. custody because Stark had provided him with a nanite suppressing
serum that prevented authorities from knowing/controlling Osborn's
whereabouts.
Norman has a meeting with a mysterious figure in which they discuss their 'deal', as seen in Civil War Front Line #7
The Green Goblin attacks and murders a group of Atlanteans, as seen in Civil War Front Line #7
Ben Urich eventually put
the pieces together, suspecting collusion between Stark and the Green
Goblin. He eventually confronts
Stark and although Tony never admits (on panel) what he had done, it seems
likely that Urich had it all correct.
Urich confronts Stark for his involvement with the Green Goblin and war provocation, as seen in Civil War Front Line #11
One of the many outcomes of Stark's use of the Green Goblin was that Norman was placed as the director of the Thunderbolts at the conclusion of the war. Stark was now Norman's boss!! And if you thought Norman was phoney before, check out the second panel below...Osborn refers to Stark as an 'American Hero'!
As Director of the
Thunderbolts, Norman had numerous interactions with Tony and for the most part
Stark treated Osborn as a subordinate that he did not like, often bossing him around like Osborn was a worthless stooge.
Stark kept Osborn on a very
short leash and he would even dose him with sodium pentathol if he wanted to
get straight answers from him (as seen below in a panel from Penance Relentless
mini series). The panel below is from Penance Relentless #4.
The Thunderbolts and the Avengers actually teamed-up along with the group known as Cyberforce to stop an alien hybrid (back inFusion 1-3). But that collaboration was short-lived and Norman and Tony would soon return to their mutually disrespectful relationship. This event marks the first time Stark and Osborn worked-together as equals toward a greater good.
Osborn would find a way to annoy Stark when he served as a guest with the Commission on Superhuman Activities (C.S.A), which happened to be investigating Stark around this time.
Stark was investigating Graviton's involvement in the death of the hero Gadget, he then presented his findings to the C.S.A. in Washington D.C. In Iron Man (V4) #23, Osborn was present during Stark's briefing as Tony shared his theory that Gadget could have been killed by her own teammate Cooper Roth (aka Paragon). The C.S.A. was dismissive of Stark's claims and the committee suggested that this case should have been closed weeks prior.
Norman plays devil's advocate to Stark and suggests that Roth could have been a 'boy unhinged' and that he may have been seeking vengeance for his friend's killer. Osborn is not seen again within the context of this case, so it is unclear what Norman's agenda was for his suggestion. Most likely he was simply trying to needle Stark, its unlikely Norman was involved with this conspiracy.
Interestingly, Norman would later slam the C.S.A. for 'not listening to him' in regards to the widespread use of StarkTech. When the Skrull Invasion was in full swing, Osborn used the media to undermine C.S.A. blame them (as well as Stark) for the invasion's lethal outcome.
Guess they'll never ask him to serve as a guest participant again...
After defeating the Skrull threat in Washington D.C., Norman goes on TV denouncing the use of Starktech, as seen in Thunderbolts #125
Osborn also managed to get a few public jabs on Stark from time to time as well prior to the invasion. When Marc Spector became a public enemy, Osborn and the
Thunderbolts were tasked with bringing him into custody. As you can see from the panels below, Osborn and Stark had different interpretations on the results of that manhunt. Osborn's use of the media to bait or slander Stark would become a consistent strategy in the years to follow.
It seemed as though both Stark and Osborn were satisfied
simply discrediting the other at press conferences, but Norman would soon
convincingly win the battle of public opinion during the Skrull Secret
Invasion. Two critical events
triggered Norman's meteoric rise to power.
The first occurred when Stark had a malfunction in his Iron Man armor that forced him to retreat from the battlefield against the Skrulls. Osborn witnessed Stark's departure and knowing full well that the media was filming every aspect of the war, he led a charge against the Skrulls. Osborn was victorious and he was beginning to be viewed as a war hero.
Norman watches Stark flee the front line and realizes that this is the opportunity to steal the spotlight, as seen in Thunderbolts #125
The second event occurred when Osborn intercepted a transmission between Deadpool and Nick Fury that contained Skrull data. Osborn used that data to his advantage and he fired the kill shot on Skrull Queen Veranke.
Norman intercepts the Skrull data transmission between Deadpool and Nick Fury, as seen in Deadpool (V2) #3
Norman delivers the kill shot on the Skrull Queen, as seen in Secret Invasion #8
Those two events placed Osborn in high favor with both the citizens and government of the United States. He was eventually brought in to speak with the President as well as testify in front of a Senate oversight committee. As expected, Osborn took both of those opportunities to slam Stark/StarkTech/C.S.A./S.H.I.E.L.D. and also propose himself as the leader of the newest peacekeeping task force called H.A.M.M.E.R. Norman was handed the keys to the kingdom as Stark took the fall failures of S.H.I.E.L.D.
To add insult to injury Osborn steals Stark's Iron Man armory and rebrands himself as the Iron Patriot. He then creates his own team of Dark Avengers. Should we remind Norman that imitation is the most sincere form of flattery??
Osborn that repurposes all of Stark's Iron Man suits into Iron Patriot suits, as seen in Invincible Iron Man #17 (bottom panel)
Norman introduces his Avengers to the world, as seen in Dark Avengers #1
This was one of my favorite panels from Dark Reign and it is perfect for this section because it shows just how much these two love to hate each other. Here's Osborn taunting Stark regarding his alterations of the Iron Man armor.
Did Osborn's obsession with the Avengers start during that statue unveiling back in Marvels #2? We may never know...
Osborn (above) at the unveiling of the Avengers statue...a party from long before Dark Reign that was featured in the retconned Marvels #2 story. He looks pretty jealous/miserable right?
When Osborn decommissioned S.H.I.E.L.D. , he created his own peacekeeping task forces and he called it H.A.M.M.E.R. As Stark vacated his position in shame, Osborn was anxious to take all that was under Stark's control, namely the database that housed all the information from the Superhuman Registration Act (ie. the secret identities of many costumed heros). It should be mentioned that this story takes place in the era of Spider-Man's Brand New Day, which involved Spidey creating a mindwipe that erased everyone's knowledge of his alter ego. Osborn was very interested in rediscovering that information.
Unfortunately for Osborn, Stark took that database with him...inside his brain. The Extremis armor that Stark used to pilot Iron Man allowed for the expansion of his neuronal capacities, meaning he could store an entire database inside his head...it also meant that now Norman really wanted Stark's head on a platter.To achieve that goal, Norman began to wage a war against Stark and his team, which included Pepper Potts and Maria Hill. Osborn attacks Stark and Hill publicly, citing that his team uncovered S.H.I.E.L.D. Executive Memo #262, a document that indicated that Hill and Stark had 'actionable intelligence' suggesting a Skrull invasion was imminent. After this decree, Osborn requested that Hill and Stark turn themselves in to authorities immediately otherwise the manhunt (and womanhunt!) would continue. There were no official charges brought against Stark, he was simply requested by Norman to turn himself in publicly at Restoration Park...Stark never showed, so the hunt began.
Tony began destroying all of his armories worldwide, and after War Machine tried to convince Stark to turn himself in, Tony refused. The two then staged a battle that led to Stark falling deep into the ocean, so Osborn sent his #1 ocean-guy after Stark, Namor. Tony is able to outsmart Namor and although he takes a beating from the Sub-Mariner, he's able to get away.
Before Stark went on the run he designed a Stark-tech armor suit for Pepper Potts, which she used to escape Osborn's forces. But Norman wanted her brought to 'justice' as well so he has H.A.M.M.E.R. monitor her location as well. They eventually find her and they realize that her Stark-tech suit is not weaponized. Norman did not believe that to be true so he ordered that a nearby commercial plane be shot down, so that he can test Potts' capabilities. He used the phoney excuse that he received intel that a Skrull sleeper agent was on that flight. Potts was able to safely land the plane, but once she was back on land, H.A.M.M.E.R. forces had her arrested. Once in custody, Osborn questioned Potts for Starks whereabouts, but she was not very helpful because she had no idea where he was. After failing to extract Stark's locale, he turned to a second request for Potts, her suit. He wanted to take her suit to gain insight into Stark's genius, but Potts would not concede and since she was under no legal obligation, Osborn was forced to free her...after he threatened her safety.
After using Namor to catch Stark unsuccessfully, Norman was forced to use another member of his cabal, The Hood. Being the kingpin of a new crime syndicate, The Hood has operatives all over the globe. Shockwave (aka Lancaster Sneed), one of The Hood's men, finds Stark but fails to apprehend him, Osborn becomes convinced The Hood has a team full of scrubs. Frustrated, Osborn requested that The Hood's partner (and former love interest of Stark), Madame Masque, speak with him privately. Osborn showed Masque the cache of Stark-tech that is still functional, he suggested to her that Stark may visit one of these caches and that that would be the key to finding him. Masque accepted Norman's proposal.
Meanwhile, Pepper Potts made her way Russia, tracking Stark's signal. After Victoria Hand uncovered that information, Norman contacted Russian Colonel Bukharin. He petitioned Bukharin for permission to enter Russian air space to shoot Potts down. The colonel declined and Norman was not very pleased by the colonel's reponse.
Eventually Madame Masque caught up to both Stark and Potts, taking them both into custody. But her jealousy got the best of her after she saw Stark kissing Potts, so she decided to torture Potts while Stark watched. Masque gets bested though, as Pepper is able to activate her Stark-tech and free both she and Tony. When Masque returned stateside, Osborn was not very pleased with her performance and he sensed that she was lying about how Tony was able to escape. Masque erroneously reported to Osborn that she'd killed Pepper Potts and recovered her armor, but Pepper was obviously not dead. Norman was going to strangle Masque because of her failure when he was interrupted by Victoria Hand. It would have been interesting to see what would have happened had they not been disturbed.
With confirmation of Stark's presence in Russia, Norman reestablished contact with Colonel Bukharin, but this time he did not ask for permission. He told the colonel that in exchange for a tip involving illegal Russian nuclear weapons, Osborn wants Stark. The colonel is forced to oblige. Tony escaped again though, this time to Afghanistan and Osborn's team is able to find his location. Osborn cannot go near Stark on Afghani territory, so he must wait until the leaves their airspace. Christopher Walsh is the H.A.M.M.E.R. agent responsible for finding Stark's signal, and he is placed in direct communication with Norman (who is in his Iron Patriot armor) as he waits for the go-ahead. Walsh had a change of heart and decided to not help Norman, he began feeding him bad information on Stark's location. Walsh's supervisor, Agent Gormley, recognized what his subordinate was doing and immediately took over command and had Walsh placed in detention.
After receiving the proper coordinates on Stark, the Iron Patriot could taste victory over his hated nemesis. Once he reached Stark, Osborn unleashed a storm of missiles and repulsor blasts, neutralizing his foe. Stark fought back slightly, but Osborn continued to pulverize Stark. Unfortunately for Norman, he could not enjoy his success for long. Pepper Potts' suit, nicknamed J.A.R.V.I.S., contacted the global media and made them aware of the fight between Norman and Tony. Suddenly, their battle was broadcasted live across the globe. Just as Norman was about to deliver his kill shot, Hand contacted him, telling Osborn it appeared as though he was going to kill Stark on live TV in cold blood. Norman is forced to pull back, but he returned to his H.A.M.M.E.R. headquarters with a nearly brain-dead Tony Stark. Osborn informed his medical staff that he wanted them to pull the plug on Stark's life support. They tell Osborn that they cannot because they do not have the power of attorney to do so, Stark's power of attorney lies in the hands of one Donald Blake...aka Thor. Stark was able to evade death.
It was at this point that we finally got to hear Osborn acknowledge why he's hated Stark for so long...
Although it is worth mentioning that throughout Osborn's hunt for Stark, he became frustrated trying to replicate certain facets of Stark-tech. Osborn even conceded that he could not mimic Stark's genius, it was interesting to see Norman concede that point aloud. With Norman's pride and his hatred for Stark, one might think he'd keep that to himself.
I think the panel below pretty much sums up the Osborn/Stark dynamic throughout Dark Reign...
Stark would later play a critical role in Osborn's downfall during his siege on Asgard. Stark disabled the Iron Patriot armor which allowed the rest of the heroes to take Osborn into custody.
Osborn would return to the public spotlight and once again use the media to slam the Avengers during his second Dark Reign (aka Dark Reign Lite). This is yet another example of Osborn using the media to attack Stark and his allies. This run by Osborn was short-lived and Norman would end up destroying himself after his Super-Adaptoid technology caused him to literally melt down.
That takes us to where we stand today. Undoubtedly these two will cross paths again and when they do, it'll be on this page!
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Honorable Mentions:
The first honorable mention to the Stark/Osborn history is the fact that Obadiah Stane once hired Mac Gargan to steal Osborn's military robotics plans...which led to Osborn losing a lucrative government contract. Since we know Stane and Stark are enemies, would this be a case where the enemy of my enemy is my friend (making Osborn/Stark allies)??
A second honorable mention comes from an alternate universe, one which took place during the events of the Skrull Secret Invasion. In the one-shot What If Secret Invasion, Spider-Man (of all people!) contacts Norman Osborn and asks him to work on a cure for the Skrull Conversion. Taking an opportunity to humiliate (and impersonate!) Tony Stark was not something Osborn would pass up.
In the end, it didn't work out well for Norman because he decided to double-cross Spider-Man (and the rest of the human race)...thus he was killed by Bucky Barnes (aka Captain America).
A third honorable mention also comes from an alternate universe, more specifically, during the second Secret War on Spider-Island. During this story, Agent Anti-Venom (Flash Thompson) uses the Goblin Formula in order to prevent Tony Stark from turning into a mindless Spider-zombie
And, as expected, the Iron Goblin was born. And for the record, the Iron Goblin died a hero!
