The Cleveland Street Phase IV Improvements was referenced in the 2008 Pembroke Area Comprehensive Transportation Plan as a desired City project.

Since 2008, the project has appeared in multiple iterations of the City of Virginia Beach’s Capital Improvement Program (CIP), first appearing in fiscal year 2012-2013, and is currently included on the City’s CIP for fiscal year 2024-2029.

The City of Virginia Beach applied for project funding through Virginia’s System for the Management and Allocation of Resources for Transportation (SMART SCALE) program in 2017 (approved in 2018). The awarded design proposed construction of a four-lane divided roadway within a 90-foot right-of-way from Witchduck Road to Independence Boulevard. This design would have required the full acquisition of 29 tax parcels.

In efforts to reduce the number of full acquisition parcels, the typical section of the proposed corridor was reduced from a four-lane divided roadway, to a three-lane undivided roadway. This reduced the overall corridor width from a 90-foot right-of-way to a 70-foot right-of-way and reduced the number of parcels proposed for full acquisition from 29 to 13. The revised design was awarded project funding in 2019.

30% design for the revised SMART SCALE design was submitted to the City of Virginia Beach by Kimley-Horn & Associates in September 2022.

Development of the project's Environmental Assessment (EA) for compliance with National Environmental Protection Agency (NEPA) began in August 2023. A draft of the NEPA document was submitted to the Virginia Department of Transportation (VDOT) and the Federal Highway Administration (FHWA) for their review and comment in April 2023.