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

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.

[4] On February 11, 1937, the western section extended westward to Gardendale, replacing SH 216.

[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.