SH 158 begins at an intersection with State Highway 302/Farm to Market Road 181 northwest of Odessa in unincorporated Ector County.

SH 158 enters the town of Goldsmith, intersecting with Farm to Market Road 866.

SH 158 was extended northeast to Abilene and west to Sterling City on January 20, 1932.

[3] On December 21, 1935, a section from Garden City to Midland was added, creating a gap.

[6] On November 19, 1938, SH 158 was extended west to 7.5 miles northeast of Ector-Winkler County line, its current end.

The two disconnected portions were finally connected on May 6, 1969 when Farm to Market Road 387, completed in 1959, was officially re-designated as SH 158 (which it was part of in 1935).

[9] On March 15, 2022, a bill was signed by President Joe Biden that added the extension of I-27 north to Raton, New Mexico, and south to Laredo to the Interstate Highway System utilizing the US 87, US 277 and US 83 corridors.

[10] A bill introduced in 2023 would explicitly designate the extension as I-27 with two auxiliary routes numbered I-227 and I-327.

SH 158-B continues to run by residential areas before turning in a more southern direction at Illinois Avenue near Midland Memorial Hospital.