In Sonic Adventure, after being defeated by Sonic and co., and with Knuckles holding on to 6 of the Chaos Emeralds, Chaos has had enough and not only effortless defeats Eggman, but also effortlessly defeats Knuckles and takes his Chaos Emeralds, proceeding to grab the final Emerald right in front of Sonic and Tails. Eggman then goes on to attack Chaos with the Egg Carrier 2, but Chaos easily dispatches Eggman and his new ship, sending him flying into the distance before Sonic defeats Chaos at last.
In Sonic Adventure 2, despite Eggman succeeding in collecting all of the Chaos Emeralds alongside Shadow and Rouge, he has to team up with Sonic and the others in order to stop the ARK from crashing into Earth.
In Sonic Heroes, Eggman wasn't even the main antagonist, as he was captured by Neo Metal Sonic and was a prisoner in his own Egg Fleet, only being saved after he helps direct Team Chaotix to his location to save him. He then later watches as the teams defeat Metal Madness/Metal Overlord.
In Shadow the Hedgehog, Eggman plays evil roles in every stage he's in, except for one stage where he becomes a hero role due to Doom's Eye being in the evil slot. Despite his attempts to defeat Shadow in some of the endings, and dying in some of the endings, Eggman appears alongside Sonic and the rest of the group in order to plead with Shadow to hand over the Chaos Emeralds to Sonic, and to keep them away from Black Doom. If you face Devil Doom long enough, Eggman reveals to Shadow that he is in fact the real Shadow, as Eggman had a robot catch Shadow during his fall to Earth, following the events of Sonic Adventure 2, which shows that Eggman does have some level of care/respect towards Shadow, even if Eggman wanted Shadow for his own uses.
In the Sonic Rush titles, Eggman teamed up with his alternate counterpart, Eggman Nega, in order to control Sonic and Blaze's worlds, and as crafty as they were, with their combined might, they were still no match for the combined power of Sonic and Blaze in super transformation, in both instances.
In Sonic Unleashed, he actually managed to defeat Sonic, even forcibly robbing him of the power of the Chaos Emeralds while draining them at the same time. Unfortunately, since he ejected the Chaos Emeralds with Sonic into space, and they fell into the planet with him, this left Sonic able to race around the planet in order to fix it and stop Dark Gaia, as well as crash through the first time Eggman has managed to create an Eggmanland.
In Sonic Chronicles, he willingly stays behind while Sonic and co. venture into the Twilight Cage, but time inside is different than time outside, so upon their return, Eggman has double-crossed the team and is now ready to shoot them down with his new armada he's assembled while Sonic was gone.
In Sonic Colors, his plans probably would have succeeded on some level had he not tried to lure Sonic and Tails to their doom, as in the end, they still managed to thwart Eggman and his Interstellar Amusement Park.
In Sonic Generations, he even went back to another dimension to recruit his former self (The game basically uses it as Classic Eggman, but we all know it's really Dr. Robotnik), and despite planning to fix the timelines and erase all of their failures, even managing to easily dispatch both Sonics, the power of the Chaos Emeralds was still too much for the Eggmen.
Now, finally, for Sonic Forces. Eggman, to be fair, was as successful as he was due to the power of Infinite and the Phantom Ruby, and the irony is that Infinite turned out the way he did thanks to Shadow effortlessly humiliating and defeating him. But the fact that Eggman not only conquered 99% of the planet, but also had several backup plans in the event something unforeseen happened, he was able to continue getting his plans into motion, literally being down to his very last trump card to face Sonic in the event that everything else had failed. It was finally his time to shine and finally time for him to be ready for anything, even stating that he's learned from his past mistakes and is finally taking measures to prevent the same mistakes from happening again.
I just really love how Eggman has done everything he can to ensure his plans were foolproof enough to ensure he could still carry on with them, even if some failures happened along the way. The fact he was willing to learn, a little, from his past mistakes, and do everything he could, is just fun to watch. Plus, he was... really vicious, in a sense. I mean, he straight up told everyone they were going to be killed, plus the threat of dropping a virtual sun on the Resistance to wipe them all out is pretty insane. Eggman was at his best, in my opinion, because of how close he was to finally succeeding in his plans, and for how thought out his plans were in this scenario.
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