Question

O knew I could ask/ask on Philip if I needed any help

Answer 1

Я знал, что  я мог бы попросить Филиппа если бы мне нужна была помощь 
I knew I could ask Philip if I needed any help

Answer 2

The sentence "O knew I could ask/ask on Philip if I needed any help" appears to be a bit unclear, but I will try to interpret it as best as I can.

It seems like the speaker is expressing confidence in being able to ask Philip for help if needed. The use of "O" at the beginning of the sentence could be a typo, and it's possible that the intended word is "I" or "I've".

So, the sentence could be rephrased as "I knew I could ask Philip if I needed any help". This suggests that the speaker trusts Philip to be supportive and helpful in times of need. It shows a sense of reliance and confidence in their relationship with Philip.