Question Summary:
Is it obligatory to pray the missed salaats in order ? What if one has much missed salaats ? When is the obligation in the order waived ? Is there any differance in the ruling of ”old missed salaats” and ”new missed salaats” ?

Question Detail:

Is it obligatory to pray the missed salaats in order ? What if one has much missed salaats ? When is the obligation in the order waived ?
 
Is there any differance in the ruling of ''old missed salaats'' and ''new missed salaats'' ?

Answer :

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In the name of Allāh, Most Gracious, Most Merciful

Assalāmu ῾alaykum wa Rahmatullāhi Wabarakātuh
 
If a person misses lesser than six Salāhs besides the Witr Salāh i.e. one complete days Salāh or less, it will be necessary upon him to perform his missed Salāhs in order before performing the current Salāh.
(Hāshiyatut Tahtāwi ala Marāqil Falāh, Pg.440, Ilmiyyah)^[1]
Once he misses six Salāh besides the Witr Salāh i.e. more than one days Salāh, it will no more be necessary upon him to perform his missed Salāh in order.
(Nōrul Idhāh, Pg.105, Qadīmi)^[2]
(Raddul Muhtār, Vol.2, Pg.68, HM Saeed)^[3]
(Hāshiyatut Tahtāwi ala Marāqil Falāh, Pg.440, Ilmiyyah)
(Fatāwa Tātārkhāniyyah, Vol.1, Pg.758, Idāratul Qurān)
If a person already missed six Salāh or more, there is no differentiation between the old and the new missed Salāh. It will still be obligatory upon him to perform Qadhā of those Salāh, however, it is not necessary to maintain the order until he completes all his missed Salāh.
(Fatāwa Tātārkhāniyyah, Vol.1, Pg.758, Idāratul Qurān)
And Allāh Ta῾āla Knows Best
Wassalāmu ῾alaykum 
 
Ml. Rayhaan Docrat,
Student Dārul Iftā
Checked and Approved by:
Mufti Ebrahim Desai
Dārul Iftā, Madrasah In῾āmiyyah