According to Independent Newspapers, discussions between the club and the experienced German coach are progressing well, with growing optimism that an agreement will be reached in the coming days.
However, sources close to the negotiations say it remains unclear whether Middendorp would return as head coach, technical director or in another capacity within the club's football structure.
Should the move materialise, it would mark Middendorp's third spell at Durban City in just 12 months.
The veteran tactician first joined the club on a short-term basis before departing after only a few months, amid reports of differing views over football operations and the club's long-term technical direction.
Despite that exit, the relationship between Middendorp and Durban City remained positive. Following Gavin Hunt's departure, the club brought him back as technical director as part of a restructured football department led by newly appointed head coach Sinethemba Badela.
That arrangement proved equally brief. Badela left after just three matches, while Middendorp also departed soon afterwards after completing what the club described as another short-term assignment.
Now, only months later, Durban City appear keen to reunite with the experienced German once again, although it remains uncertain what responsibilities he would assume if an agreement is finalised.
His possible return comes at a crucial time for the KwaZulu-Natal outfit, who are preparing for a demanding 2026/27 campaign. After lifting last season's Nedbank Cup, Durban City will compete in the CAF Confederation Cup while also aiming to establish themselves in the Betway Premiership following promotion.