In this case it is best if first you trim your hair, and shave it after the second umrah, though doing two Umrah like this in a row is not from the sunnah.

I have the intention of performing umrah soon in sha Allah and upon completion i will get my head shaved to receive the maximum sawaab. After that i wanna perform another umrah for one of my deceased. So after performing 2nd umrah wat do i do regarding my removal of hair as i have already shaved my head after the 1st umrah. please help with this.

Hajj and Umrah | October 3, 2015 3:14 am
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We arrived in Mina on the night of the 8 the of dhulhijjah. We prayed fajar dhuhr and asr of the eight of dhulhijjah hijjah in Mina and the magharib and isha of the 9 the of dhulhijjah hijjah thereafter we left to Arafat, in the night itself. Should I offer any sacrifice or penalty?
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 I want to ask if a person went for umra and after doing tawaf he had  some emergency and he left umra incomplete and came back to his house  without sae and removed ihram.. What will be the ruling? Does doing dam is enough or he has to complete or repeat his umra? Plz clearify.