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Grace Hopper Award
| Year | CTO | District |
| 2021-22 | Matt Flood | Goose Creek ISD |
| 2020-21 | Bryon Kolbeck | Lewisville ISD |
| 2019-20 | Cindy Bingman | Aldine ISD |
| 2018-19 | Frankie Jackson | Cypress-Fairbanks ISD |
| 2017-18 | Hector Reyna | Socorro ISD |
| 2016-17 | Adam Feind | Northwest ISD |
| 2015-16 | Kevin Schwartz | Clear Creek ISD |
| 2014-15 | Miguel Munoa | Laredo ISD |
| 2013-14 | Steve Young | Judson ISD |
| 2012-13 | Lenny Schad | Katy ISD |
| 2009-10 | Frankie Jackson | Goose Creek ISD |
| 2008-09 | Bob Daughrity | Pasadena ISD |
Team Award
| Year | District | CTO |
| 2021-22 | Midlothian ISD, | Leslie Garakani |
| 2020-21 | Hutto ISD | David Oestreicher |
| 2019-20 | San Antonio ISD | Kenneth Thompson |
| 2018-19 | Austin ISD | Kevin Schwartz |
| 2017-18 | Region 11 ESC | Rory Peacock |
| 2016-17 | Spring Branch ISD | Venu Rao |
| 2015-16 | Northwest ISD | Adam Feind |
| 2014-15 | Cypress-Fairbanks ISD | Frankie Jackson |
| 2013-14 | Clear Creek ISD | Kevin Schwartz |
| 2009-10 | Irving ISD | Alice Owen |
| 2008-09 | Lewisville ISD | Greg Veale |
Tech Savvy Superintendent
| 2021-22 | Dr. Holly Ferguson | Prosper ISD |
| 2020-21 | Dr. Michael Hinojosa | Dallas ISD |
| 2019-20 | Tim Harkrider | Willis ISD |
| 2018-19 | Dr. Jose Espinoza | Socorro ISD |
| 2017-18 | Mike Kuhrt | Wichita Falls ISD |
| 2016-17 | Dr. Jamie Wilson | Denton ISD |