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May men distribute Matanos Laevyonim to female paupers and vice versa: 
The gifts may be sent to any Jew whether male or female. Thus a man may give to a female pauper and vice versa. It is permitted for even food to be given as Matanos Laevyonim from a man to a women and vice versa.
May one give Matanos Laevyonim to a pauper that is celebrating Purim on a different day?
- Example A: Can one living in Jerusalem give Matanos Laevyonim to a pauper that kept Purim on the 14th?
- Example B: Can one who is keeping Purim on the 14th give Matanos Laevyonim to a pauper who will be keeping Purim in Jerusalem on the 15th?
Example A: If one who is celebrating Purim on the 15th gives Matanos Laevyonim to a pauper that already celebrated on the 14th, and is thus no longer celebrating Purim, then he does not fulfill his obligation.
Example B: If one who is celebrating Purim on the 14th gives Matanos Laevyonim to a pauper that will celebrate Purim in Jerusalem on the 15th, he does not fulfill his obligation. If however one sends the money on the 14th, or prior to the 14th, and it will not arrive to the pauper until the 15th, then some Poskim rule it is valid. Other Poskim however rule it is invalid as in actuality the Mitzvah was not done on the 14th which is the day of Purim for the giver.
May one who lives out of Jerusalem give Matanos Laevyonim to a Jerusalem based charity fund that will distribute the funds on the 15th?
This matter is disputed amongst Poskim as explained above in Example B.
May one who lives in Jerusalem give Matanos Laevyonim to a charity based outside of Jerusalem that will distribute the funds on the 14th?
No, as explained above in Example A.
 Rama 695/4
 However Mishloach Manos must be given from a male to a male and female to a female. The difference is that by money given for Matanos Laevyonim there is no suspicion that he is giving it to her because they are already engaged, as it is only common to give gifts and presents and not money. Likewise it will not appear like Kedushin money, being there are no set witnesses. However by Mishloach Manos it will cause a question of betrothal because people will think he is sending her the gifts because she is already engaged to him. [M”A 695/15] Alternatively the reason it is permitted by Matanos Laevyonim is because it is for charity purposes, and if we would forbid this paupers would not have how to live. [Olas Shabbos 695/3 brought in Kaf Hachaim 695/61]
 Elya Raba 695/14; P”M 695 A”A 15; M”B 695/27; Kaf Hachaim 695/60
 Ikareiy Hadaat 36/24
The reason: As the present must reach the pauper on the day of his celebration, as the purpose is to increase in his Purim Seuda on that day. [ibid]
 Ikareiy Hadaat 36/24 brought in Mishneh Halachos 4/87; Tzitz Hakodesh 56; Divreiy Moshe 1/38; Kinyan Torah 4/86; Az Nidbaru 6/80; Minchas Yitzchak
 The reason: As the we follow the recipient of the Matanos Laevyonim and since he receives it on the day of his Purim the giver fulfills his obligation.
 Kaneh Bosem 2/33; Chazon Ish brought in Teshuvos Vihanhagos 1/104
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