What if Indrajit fights Karna? Who will win?
Karna has his divine kavach (armour) and earings and Indrajit has his flying chariot and his mayavi (illusions).
In a sense both Karna and Indrajit share some similarities; both of them were great warriors who could not be defeated in a fair battle. Karna was killed, when he was defenseless, while trying to remove his chariot well, and Lakshman had to disrupt Indrajit's Yagna before sunrise, and then fight him, else he would have had been invincible. Karna implored Arjun and Krishna that it was not fair to strike at an enemy when he is without arms, while Indrajit called Lakshman a coward, when the latter attacked him unarmed during the Yagna.
Both of them served their rulers well, Karna undertook a Digvijaya Yatra for Duryodhana, subduing many rulers like Bhagadatta, Rukmi, and conquered most of North, South and Eastern parts of India. Indrajit conquered the heavens itself, and he got his name from the fact that he conquered Indra himself, rendering him unconscious, and carrying him away, before Brahma intervened. Both of them were known to be good husbands to their wives Sulochana and Vrushali respectively. If Karna was protected by his Kavach( divine armor), Indrajit drew his strength from the Yagna he conducted before every battle.
Now let us see how these two great heroes, would square up in a one to one battle.
Indrajit had the 3 most powerful weapons ever, the Brahmanda Astra( of Brahma), Vaishnava Astra and Pashupatastra. Karna had the Brahmanda Astra, Brahmastra, Brahmashira Astra, as well as the Rudra, Shiva, Maheswhara Astra. He also had formidable Astras given to him by Indra, Surya, Vayu, Agni, Varuna. Above all he had the Vijaya, a bow so powerful , that not even the Pashupatastra would have impacted it. If Karna and Indrajit fought head to head, the result would have been inconclusive, as both of them were powerful warriors, equipped with some of the deadliest weapons. However considering that Karna was cursed to forget how to deploy the Astras when it was needed most, Indrajit would be having the advantage here. Indrajit's strength was not just the dazzling array of weaponry he had, it also lay in the fact that he knew how to use them effectively. This was the reason why he was able to defeat both Ram and Lakshman, which even his father failed to do so. It must be noted that each of these Astras had their own mantra to deploy them, sort of like the codes you use to deploy a nuclear missile, failing which they would be practically useless. Indrajit knew them well, Karna also knew them, but the fact that he would forget them when needed would give the former a decisive edge here.
Regarding Indrajit's tactics of Maya, it must be noted that Karna successfully defeated and killed Ghatotkacha who had used the same tactics. Karna was in possession of the Mohini Astra, which would dispel any Maya in the vicinity. So even if Indrajit had used all his tactics of Maya with him, Karna would have countered it with the Mohini Astra. Also Karna had to face a far more formidable battle with Ghatotkacha at night, when the Asuras are known to be even stronger. Ghatotkacha, unleashed hell on the Kaurava forces, raining down fire, hail stones, storms, and in each case, Karna managed to counter it. Even Indrajit's famous Naga Pasha, which he used to bind Rama and Lakshmana, and render the latter unconscious, would not have worked against Karna. He himself had the Naga Pasha, that would have countered Indrajit's, and the even more deadlier Naga Ashtra, that never missed it's aim. Karna also possessed the Tvastar Astra, that would often cause confusion in the enemy ranks, and make them kill each other. And above all, Karna had the Vasavi Shakti given to him by Indra, that was infallible, which he intended for Arjun but was forced to use against Ghatotkacha. In a one to one battle between Karna and Indrajit he would have surely used the Vasavi Shakti against Indrajit's Maya tactics.
It would be a formidable battle between Karna and Indrajit, both of them great warriors, both known for their mastery of weapons, but as pointed out, the curse on Karna by which he would forget how to use the Astra at the right time, would be giving a decisive edge to Indrajit.