I would give Cherry and her friend the "Girls Who Like Bad Boys" award. They both were attracted to the Greasers for the wrong reasons. If that were not the case, why else would she tell Pony not to expect her to talk to him at school?
Darry would be given "The Rock and a Hard Place" award. He wanted to better himself outside of the confines of the gang, but family situation dictated otherwise.
Pony and Johnny would be given the "Literate" award as they both had so many daily connections to literature.
Dally would be given the "Coward's Way Out" award as he chose to let the cops kill him rather than fight his way out of the only life he knew.
Johnny would be given the "Devil You Don't Know" award as the uncertainty of life on the run was better and safer than his life at home.
I'd give Dallas an award -- I'd give him access to a mentor who has the same sort of background he does to show him that there is hope and that someone with his charisma can make it in life (obviously this has to be before he gets killed).
I'd give Randy an award of counseling to help him get through his grief and his sort of ambivalent feelings about his dead friend Bob.
Fun question. It would be pretty easy to give Ponyboy and Johnny awards for selfless heroism, but they are already rewarded, in some ways, within the book. The honor they receive in the newspaper isn't much, compared to what they did, but I'm going to skip them anyway. Too easy.
I'd give Darrel an award, in the form of a college scholarship, for caring for his brothers after his parents died. He could have left them behind to struggle alone in foster homes, but he put off his own goals, stayed home, and kept his family together.
I'd give Cherry and Randy awards for making an effort to forge communication with kids who are their traditional enemies. They both, especially Cherry, risk becoming victims of violence when they go talk to greasers. Their award would be...um...safe passage on the streets, both in their side of town and on the greasers' side of the tracks.
Soda deserves an award for standing by his girlfriend, even when she cheats on him, and for being a peacemaker between his brothers. I'd give him a free trip to Florida so he can try to patch things up with Sandy.
Finally, I'd give Ponyboy's English teacher an award for pushing Ponyboy to achieve when he is failing at the end of the book. It would be easy for the teacher to give up, but he does not. He should be honored in the newspaper, and he should receive a big grant that will help him buy better classroom materials. Hooray for English teachers!