Neo is in his prime. Tony has his Bleeding Edge armor. Fight takes place on a simulated Titan within the Matrix, giving both access to their fullest abilities. Each arrive at the battlefield knowing an opponent is there and have five minutes to mentally prepare themselves for the coming conflict. Start standing facing one another from fifty meters apart. In character but think the other one is an agent of The Matrix/Thanos.
Neo (The Matrix) VS Iron Man (Marvel Cinematic Universe)
This is tough. Neo might be too fast and Tony too durable with the nanites.
Neo could possibly blitz him. His flight was fast enough to break skyscraper glass and leave tons of cars floating and destroyed in his wake. Whether he'd be able to put him down is another question.
Erm, Neo. This is inside the Matrix, which gives Neo a massive advantage over his foe in terms of speed and versatility. If Tony goes into CQC with him, he'll get taken out with ease.
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