I also want to boost his confidence so that he will be able to speak up when he feels that he needs help. I am desperate and concerned that he may have to repeat third grade. How can I help him?
Talk with your son's teacher about your concerns. Make sure that she is aware that your son seems to be struggling and that he may not be speaking up when he needs help. The teacher can direct you to workbooks and other materials that will enable you to reinforce what your son is doing at school. Also talk with the school counselor. She may be able to give your son some individual time to work on his self-esteem and his assertiveness skills.
It's wonderful that you're willing to work so hard to help your son. Keep in mind, though, that children often work better for other people than for their parents. If you find that your work time with your son becomes a battle, look for someone else to help him with his work. There may be a high-school student in your neighborhood who would work with your son, or perhaps there are tutors available through your public library or a church or community center.