Excavations have unearthed sherds of the grey painted ware (c. 1000 BC) that some archaeologists associate with the age of the Mahabharata, but no coherent settlement traces have been found. Some locate Indraprastha in the Purana-Qila area.

The earliest architectural relics age back to the Mauryan Period (c. 300 BC); since then, the site has seen continuous settlement. In 1966, an inscription of the Mauryan King Ashoka (273-236 BC) was discovered near Srinivaspuri. Two sandstone pillars inscribed with the edicts of Ashoka were later brought to the city by Firuz Shah Tughluq in the 14th century. The famous Iron pillar near the Qutub Minar was commissioned by the emperor Kumara Gupta I of the Gupta dynasty (320-540) and transplanted to Delhi at some time in the 10th century. Eight major cities have been situated in the Delhi area. The first four cities were in the southern part of present-day Delhi.

The more recent city is believed to be made up of seven successive cities, the remains of some of which can still be seen on the ground. They are as under:

1. Qila Rai Pithora built by Prithvi Raj Chauhan, near the oldest Rajput settlement in Lal-Kot
2. Siri, built by Alauddin Khilji in 1303
3. Tughluqabad, built by Ghiyazudin Tughluq (1321-1325)
4. Jahanpanah, built by Muhammad bin Tughluq (1325-1351)
5. Kotla Firoz Shah, built by Firuz Shah Tughluq (1351-1388)
6. Purana Qila built by Sher Shah Suri and Dinpanah built by Humayun, both in the same area near the speculated site of the legendary Indraprastha (1538-1545)
7. Shahjahanabad, built by Shah Jahan from 1638 to 1649, containing the Lal Qila and the Chandni Chowk.