1- Bruce and Tim. Arguably the most successful Dynamic Duo. Tim's presence gave Batman balance in his life and prevented him from going down a self-destructive path after Jason's death. They worked every well together and at one point, they ended all crime in Gotham. It also re-enforced Batman's belief that people are capable of good, as Tim became Robin not because of a tragedy, but because he wanted to do good. This turned a smart kid into a hero and turned a damaged hero into an even better hero.
2- Bruce and Dick. The Original Dynamic Duo. In a similar case to Tim, Dick's presence gave Batman a better outlook on life, and that being Batman doesn't have to be as dark and tragic as he originally thought it was. The fact that Batman was able to turn Dick's life around after the death of his parents renewed Bruce's confidence about Batman's power to give people hope.
3- Dick and Damian. This team established a new dynamic between Batman & Robin. Batman became the lighthearted one while Robin was the darker one. This team up gave Damian a new purpose in life as a hero instead of an assassin, while Dick became more confident as Batman, and started to see himself more worthy of the cowl and worthy of filling Bruce's shoes. This team is basically the reason for Damian rebelling against his mother and becoming a full blown hero instead of ruthless assassin.
4- Bruce and Damian. When they first teamed up they struggled a lot due to the fact they both have the same dark and brooding nature. While Damian enjoyed the trust that Dick gave him, Bruce was not as trusting which caused some conflict. But this team up allowed Bruce to have a better understanding of his son that damaged by mother, and this allowed to grow as a father and he became more trusting. Damian on the other hand, the desire to impress his father, despite their struggles, allowed him to re-enforce everything Dick built in him, and so he grew even more as a hero till the bitter end.
5- Bruce and Jason. While it started full of potential, it quickly crumbled. Batman recruited Jason because he both missed Dick's presence, and at the same, like he did with Dick, wanted to make a difference in a troubled child's life. And he did, the problem is, Jason's troubles were much worse than Dick. Jason was full of rage, and it wasn't long until he became rebellious, reckless and ruthless. Batman couldn't temper Jason like he did with Dick, and that led to his death, which Batman considers to be his biggest failure.
6- Bruce and Stephanie. This was a disaster straight from the beginning. First off, Bruce never wanted Stephanie to be Robin, but due to her persistence and smart ass yet cheerful nature, she grew on him, though he still had his doubts. He let her become Robin without telling Tim, who was her boyfriend, which strained his relationship with Tim. But he was also extremely harsh on her, harsher on her than any other the other Robin, causing her to resent him and rebel the same way Jason did. Batman didn't give her any second chances, and fired her when she screwed up. In an attempt to regain Batman's trust and impress him, Steph tried to use one of his contingency plans to end organized crime in Gotham. However, she messed up and it led to a huge crime war in Gotham and ultimately her torture and death at the hands of Black Mask, a death that haunted Batman almost as much as Jason's.
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