Welcome to our speculative stadium, where legends duke it out and winner takes all! All what? No one knows! We’re just here to have fun!
Fun’s probably not on either of these two’s radar, though. These kids have been through a lot - is that a prerequisite to being part of the Batfam? That’s a whole other discussion by itself!
This is focusing on a battle of wits and skill between two highly trained, highly perceptive, and sometimes morally ambiguous combatants.
Which of these two seriously intense fighters would win in an all out duel? Give us your reasoning and vote, below!
I really really really like Damian.
He was the first Robin whose stories I read in Super sons.
And I really really like Cass Batgirl.
And unless some telepath messed up her head.
She’s the best.
It could be anyone in that slot against Cass, up to and including Batman himself, and it’s no contest. Among non-metahumans, Cass is the greatest fighter in the DCU.
I like Damian. I also like Cass. I like Cass more than I like Damian, but don’t believe that my own preferences should dictate who would win in a fight. For example, I also love Jason Todd just as much as I love Cass, yet fully acknowledge that Cass would beat him like a drum. So know that it is with no bias that I say: the only possible reason that Cass would not wipe the floor with Damian is if she felt bad about fighting a kid.
(As a side note, I would heavily contest the characterization of Cass as “morally ambiguous.” She’s one of the most moral characters in comics.)
Both were raised by assassins. But there the similarities end. Damian was raised by those who drilled in his head his innate superiority over everyone else. Ras al Ghul and Talia made certain he saw himself as a type of royalty, that his desire to win at any cost was tampered by a healthy self preservation instinct. He has his father’s ability to plan ahead and in probably the most deadly of all the Robins. Cassandra was raised to see herself as less then human, as a weapon and nothing more. For her the mission is all and if dying is called for she is ready to cross that line. In a toe to toe fight she would be willing to do things that would cause Damian to hesitate.
Cass wins its not even a fight, remember in Stephanies time as batgirl Damian kept asking about Cass clearly want to fight with or learn from her, Damian knows he can’t beat her
Ah, thank you for another tantalizing bout this week!
Damian has much more to learn, and from what I have read about Cassandra Cain… Well… This does accurately show my reaction to what she’s capable of doing…
Cassandra should win. It shouldn’t even be a contest. That said, they’ve had Deathstroke job for Damian, so there’s always the possibility that the he might win by editorial fiat. That’s the only way it could happen, though.
That’s a whole other discussion by itself! 
