How to say he tried more than once, only to fail. 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一度一度(ichido) (n-adv) once/one time/on one occasion/one degree/one tone/one musical intervalな(na) (prt) connects adj to noun/indicates emotion or emphasis/command/prohibitionらずno dictionary result, likely a conjigated verbno dictionary result, likely a conjigated verb試み試み(kokoromi) (n) trial/experimentたがたが(taga) (n) hoop/binding、(、) Japanese comma失敗失敗(shippai) (n,adj-no,vs) failure/mistake/blunderに(ni) (prt) indicates such things as location of person or thing, location of short-term action, etc.終(owari) (io) the endわ(wa) (prt) indicates emotion or admiration/adds a female middle aged feel at the end of a sentenceったno dictionary result, likely a conjigated verbno dictionary result, likely a conjigated verb。(。) Japanese period "."    
kareha ichido narazu kokoromi taga 、 shippai ni owa tta 。
Grammer form日常会話 (Casual form)Casual form (nichijoukaiwa)
everyday casual language, commonly used between friends and family.
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