The Pirates' men's basketball team's 3-4 start to the 2019-20 season was not what they envisioned, but as the saying goes, "It's not how you start, it's how you finish." Ventura won 13 of its final 15 games, including a 12-game winning streak to post the first undefeated Western State Conference North Division record in 12 years as they captured their fifth straight conference crown. VC won the Antelope Valley College Tournament in early December and defeated eventual state elite eight qualifiers Riverside and Los Angeles Valley in posting a 21-8 overall mark in another successful season.
The Pirates swept the WSC North post-season award with Timothy Turner was named conference Most Valuable Player honors and Tone Patton earned the WSC North's Defensive Player of the Year Award. Ninth-year head coach Joey Ramirez was named the conference Coach of the Year for the fifth straight season. Dayshone Henry and Shulton Tobin earned first team All-WSC accolades and Dayveon Bates was named honorable mention all-conference. Turner was named first team all-state by the California Community College Men's Basketball Association and Henry earned honorable mention all-state honors.
The Pirates earned the No. 9 seed in the CCCAA Southern California Regional Playoffs, falling on a last-second shot in overtime.
Henry, who averaged a team-high 18.8 points and 8.7 rebounds per game was named the team's MVP and Donavan Williams' work in the classroom earned him the team's Scholar Athlete Award.
| VC Men's Basketball 2019-20 |
| 21-8 (12-0) |
| Western State Conference North Division Champions |
| SoCal Regional Playoffs No. 9-Seed |
| CCCMBCA All-State |
| Timothy Turner, 1st Team |
| Dayshone Henry, Honorable Mention |
| Western State Conference North Division |
| Timothy Turner - Most Valuable Player |
| Tone Patton - Defensive Player of the Year |
| Joey Ramirez - Coach of the Year |
| All-WSC 1st Team |
| Dayshone Henry, Tone Patton, Shulton Tobin, Timothy Turner |
| All-WSC Honorable Mention |
| Dayveon Bates |
| Team MVP - Dayshone Henry |
| Team Scholar Athlete - Donavan Williams |