Channel 65 actually began as a leased cable channel (Channel 32 on what is now Comcast Cable in Henrico County) running religious programming around 1980. Christal Inc, run by James Campana, the company leasing the channel later decided they wanted a full time broadcast station. They later applied for Channel 65 in Ashland. But it took most of the 1980s to get the station on the air. First Christal had to pay off a competing applicant, then Hanover County denied the company permission to construct a tower in their county. So the station was forced to build a tower site in neighboring King William County. The station finally signed on in 1990 as a religious television station with the calls WZXK owned by Christal Broadcasting. Originally offering only Christian programs such as The 700 Club and Trinity Broadcasting Network's Praise The Lord, it began branching into general entertainment programs in the later afternoon/early evening hours over the next few years. By 1993, WZXK upgraded to 24-hour operations and increased non-religious programming to occupy about a third of its daily schedule. For a while, the station was calling itself "Fun 65".
Two years later, Bell Broadcasting, LLC purchased WZXK and affiliated it with the fledgling WB network, changing the calls to WAWB. In 1997, Bell Broadcasting sold the station to Virginia based Lockwood Broadcasting, which negotiated with WRLH to move the UPN affiliation from being secondary on WRLH to primary on WAWB. With this move, WAWB took the temporary calls of WZYX and shortly after took the current calls of WUPV.
Shortly after this move, WRLH owners Act III Broadcasting was purchased by Sinclair Broadcast Group, which was in the midst of changing many of its stations to WB and was legally enjoined from doing so in Richmond due to the contract signed by Bell Broadcasting after much trying. After the affiliation swap, WB programming moved to NBC affiliate WWBT-TV in 1998, where programming aired in overnight hours through the summer of 2006 (this arrangement led to Richmond being one of the worst markets for WB network ratings. One problem was that WWBT could not carry the entire WB prime time line up due to time limitations, so the station opted not to carry WB's Friday Night schedule), while Kids WB programming was cleared on WRLH.
In 1998, WUPV carried PAX TV as a secondary affiliate until PAX placed a 24-hour cable channel on most cable systems in Richmond. (Pax later evolved into ION Television)
In the early 2000s, several attempts to launch a standalone WB affiliate in the market fell through, among them low-power channel 48 (later reallocated and now Daystar-owned WRID-LP) and full-power channel 19 (reallocated to Charlottesville and now CBS affiliate WCAV).
Some UPN affiliates aired selected shows from UPN such as America's Next Top Model, or Veronica Mars from the previous week during the weekend. WUPV was one of the affiliates used to air Veronica Mars on Saturday Morning at 11AM but for unknown reasons quickly replaced it with infomercials in early June 2006.
WUPV was known on air as UPN 65 from 1997 to 2002. From 2003 to the network switch to the CW in 2006, it was known as UPN Richmond.
On May 29, 2006, a month after the announcement, WUPV started airing commercials promoting their CW affiliation, which took effect on September 18, 2006. WUPV, formerly locally known as UPN Richmond, became CW Richmond at midnight on July 27, 2006. However, the station continued to carry UPN programming (except for their weekend movie) until the network's closure.
In 2006, the station was sold to Southeastern Media Holdings, a division of Raycom, and WUPV moved its operations into Raycom's WTVR-TV’s Broad Street studios in Richmond. A new website for WUPV was launched a short time afterward.
In November 2007, Raycom purchased NBC affiliate WWBT from Lincoln Financial. That purchase closed on April 1, 2008. Raycom was prohibited from owning two major "Big Four" network affiliates (ABC, NBC, CBS, Fox) in the same market so CBS affiliate WTVR-TV was chosen for divestiture (the first proposed buyer turned out to be the Sinclair Broadcast Group, but the US Department of Justice refused permission for the sale under a consent decree with Raycom ). Raycom/Southeastern will keep WUPV. WUPV's operations will move to WWBT's facility as soon as the sale of WTVR is finalized.
On March 5, 2007, WUPV launched a 35-minute weekday newscast produced by WTVR-TV, called CW News @ 10 , to compete against WRLH's newscast, Fox News @ 10, produced by WWBT-TV. Weekend newscasts began on October 20, 2007.