Nothing is required of the one who departed from Makkah to Madinah or Jeddah after completing the Umrah and before entering ihram for Hajj

Rather, his departure has waived the sacrifice required for Tamatu’, because it nullified his Tamatu’ – as he has traveled a short or longer distance according to the Hanabilas – but his leaving has no effect on his Hajj.

As for where to enter Ihram after leaving Makkah: Since he has gone outside the meeqat, he should enter ihram when passing through the meeqaat or wherever that is adjacent to it.

When  he visited Madina Al Munawwarah  in that condition, he is like the dwellers of Madinah. They should enter ihram from dhul hulayfah. 

By that, he has become a mufrad and has been excluded from the attribute of tamattu’. Therefore, the slaughtering for tamattu’ is waived for him, except in the case he passes through the meeqaat after leaving for Madinah or elsewhere without putting on ihram. He also enters Makkah without entering ihram, then he has to slaughter an animal due to passing the meeqat without putting on ihram.