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Originally Posted by GoldMutant
They have fought together against the brothers a few times and as Wesley said they are extremely rare to encounter. Some are in the later seasons of the show though, so you'd have to rewatch the series to find out.
With that said, there should have been more with Shred-head and Krang teaming up, those fights are near classic to catch. Perhaps one fight in the video games could have been a double battle on the 16-bit consoles like Dracula and Death in Castlevania: Portrait of Ruin.
Then again, I'm getting off topic. This should have been done at least once per season to make the fights special. A total of 8 to 9 fights could have happened, but they'd be highlights. 
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I really wanted them to fight together more often. Krang himself rarely fought and it's even more rare for him to fight with Shredder. I just found it weird the two main villains of the show rarely fought the Turtles in direct combat.
I actually would have wanted to see that in the games. Shredder was usually the final boss, which also makes me think that some people think Shredder is the true main villain, but there were a few games where Krang was the final boss instead of being the second-to-last boss. That would be cool if you could fight both Shredder and Krang together. They were the main villains of the show after all.