Yes, he did.
Php 3:6 Concerning zeal, persecuting the church; touching the righteousness which is in the law, blameless.
Php 3:7 But what things were gain to me, those I counted loss for Christ.
Php 3:8 Yea doubtless, and I count all things but loss for the excellency of the knowledge of Christ Jesus my Lord: for whom I have suffered the loss of all things, and do count them but dung, that I may win Christ,
Php 3:9 And be found in him, not having mine own righteousness, which is of the law, but that which is through the faith of Christ, the righteousness which is of God by faith:
Paul learned the same thing that Job learned. God said that Job was upright, righteous, because he did everything that God commanded him to do. That is why Job stood firm in his innocence. But Job had to learn that it was not by his own righteous doings that he would see his Redeemer, but by the grace of God whom he had put his faith in.
God said to Job, when you can do all the things I can do, then I will admit to you, that your own right hand [righteous works] can save you.
However, neither Job or Paul claimed to be sinless, only that they obeyed the commandments and were blameless under the laws that God had given to them.
imo....
God did not give a law, any commandments, that man was incapable of doing, the problem was man being weak in the flesh, in most cases, did not do it. And in other cases even when they did do it, they were arrogant in thinking that by doing it they would be saved. When in reality it was only by God's grace through faith that they would/could be saved.
How did Jesus do the Law perfectly? He obeyed every jot and tittle that pertained to Him, giving all the glory to His Father in heaven. We know that He was sinless, so never would have been required to make atonement for sin, as Job and Paul would have been required to do.