How to say he tried several times, but did not succeed. in Japanese

1)彼(kare) (ok) that , or something understood without naming it directly)/that person/over there/hey/eh?/thatは(ha) (int) indicating a subject/yes/indeed/well/ha!/what?/huh?/sigh何度何度(nando) (n) how many times?/how often?か(ka) (prt) indicates question/indicates choice, doubt, etc.no dictionary result, likely a conjigated verbno dictionary result, likely a conjigated verbんだんだ(nda) (exp) the expectation is that .../the reason is that .../the fact is that .../it is that ...が(ga) (prt) indicates sentence subject/indicates possessive/but/however/still/and成功成功(seikou) (n,vs) success/hitしなかったしなかった(shinakatta) (v) didn't do。(。) Japanese period "."    
kareha nando ka chou ndaga seikou shinakatta 。
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Translation by mookeee
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