The initial expressway, from Jalan Boon Lay to the East Coast Parkway, was completed in June 1982.

[6] The PIE was initially conceived by the Public Works Department as part of plans to expand Singapore's road network in the 1960s to cope with a predicted large rise in traffic volume over the next two decades.

[11] Work on the 8-mile (13 km) long section between Jalan Anak Bukit and Thomson Road began in March 1970.

[17] Work was started in November 1977 to expand Whitley Road to six lanes, along with the construction of a grade-separated interchange to link it with the PIE.

[11] On 10 January 1981, the 10-kilometre (6.2-mile) segment of the PIE between Jalan Eunos and the East Coast Parkway was officially opened by Teh Cheang Wan, the then Minister of National Development, having cost $50 million to construct.

[20] The section of the expressway between Upper Bukit Timah and Corporation Road was opened soon after on 31 January 1981 by Lee Yiok Seng, the Parliamentary Secretary of National Development at the time.

[23] From 1983 to 1984, two lanes, one in each direction, were added to the 16.4-kilometre (10.2-mile) section of the expressway between Mount Pleasant Road and Jalan Boon Lay.

To alleviate this, portions of the PIE, such as the Woodsville interchange and the intersection with the Central Expressway, were upgraded in May 1991 at a cost of $180 million.

As the amount of traffic using the KJE and PIE to the Jurong industrial estate increased, the Land Transport Authority upgraded the stretch of the PIE between Tengah Flyover and Tuas Road to a four-lane dual carriageway from the previous three lanes.

Beginning July 2011, the stretch of the PIE between Clementi Avenue 6 and Adam Road was widened; one lane was added to both sides of the expressway.