2023
- Madison Coleman, Chicago Roofers JATC
- Hailey Cruz, Pine Roofing
- Priscilla Diaz, Riddiford Roofing Company
- Diego Garcia, Bennett & Brosseau Roofing, Inc.
- Mirabellah Hernandez, Korellis Roofing, Inc.
- Alexandra Jara, Olsson Roofing Company, Inc.
- Lazo Knezic, Korellis Roofing, Inc.
- Aidan Love, Sterling Commercial Roofing Inc.
- Anna Magana, Bennett & Brosseau Roofing, Inc.
- Raymundo Martinez, Olsson Roofing Company, Inc.
- Nolan Morrisey, Knickerbocker Roofing & Paving
- Vanessa Rodriguez, Preservation Services, Inc.
- Angelina Sanchez, Bennett & Brosseau Roofing, Inc.
- Nicholas Trujillo, Olsson Roofing Company, Inc.
- Connor Tulley, Riddiford Roofing Company
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2022
- Jennalys Blanford, Knickerbocker Roofing & Paving
- Michelle Blanford,Knickerbocker Roofing & Paving
- Garrett Blankenship, Combined Roofing
- Ella Coleman, Combined Roofing
- Alexandra Cruz, Pine Roofing
- Fernando Delgado, Riddiford Roofing Company
- Ryan Klickner, M.W. Powell Company
- Sandra Molina, A-1 Roofing
- Vanessa Morales, Local 11
- Lynett Ortiz, Bennett & Brosseau Roofing, Inc.
- Ian Perez-Santilan, M.W. Powell Company
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2021
- Bianca Arriaga, Pine Roofing
- Emily Arriaga, Pine Roofing
- Kasandra Bahena, Ridgeworth Roofing
- Jasmeene Guido, Anderson & Shah Roofing, Inc.
- Arturo Lopez, Anderson & Shah Roofing, Inc.
- Alejandra Martinez, Waukegan Roofing
- William Rauch, Ridgeworth Roofing
- Edwin Rosendo, Olsson Roofing Company, Inc.
- Daniel White, All Sealants
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2020
- Julissa Acosta, Anderson & Shah Roofing, Inc.
- Abby Baetzel, Sullivan Roofing
- Heather Blankenship, Combined Roofing
- Joseph Brueck, Olsson Roofing Company, Inc.
- Madison Bylak, IWS
- Brenda Huerta, Anthony Roofing
- Eduardo Jara, Olsson Roofing Company, Inc.
- Bridget Jeffries, Waukegan Roofing
- Joanna Lopez, A-1 Roofing
- Magaly Muro, Chicago Park District
- Evelyn Perez, Bennett & Brosseau Roofing
- Vena Prudent, Vac-It-All Services
- Anthony Ruiz, Bennett & Brosseau Roofing
- Kayla Strezo, M.W. Powell Company
- Alexandria Trujillo, Olsson Roofing Company, Inc.
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2019
- Jason Cler, Ridgeworth Roofing
- Megan Jeffries, Waukegan Roofing
- Artur Konopka, Crowther Roofing & Sheet Metal
- Itzel Murillo, Sager Sealants
- Jordan Roque, M.W. Powell Company
- Brian D. White, All Sealants
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2018
- Jackson Cler, Ridgeworth Roofing
- Alex Dubin, Roofers Apprenticeship Center
- Kylie McCarthy, Jones & Cleary Roofing
- Breanne Morrissey, Knickerbocker Roofing & Paving
- Lizett Muro, A-1 Roofing
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2017
- Jesus Barajas, M.W. Powell Company
- Tiffany Blankenship, Combined Roofing
- Ronan Morrisey, Knickerbocker Roofing & Paving
- Alyssa Moss, Bennett & Brosseau Roofing
- Payton Roque, M.W. Powell Company
- Auston Walton, Olsson Roofing Company, Inc.
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2016
- Cayley Mason, Olsson Roofing
- Aimee Muro, A1 Roofing Company
- Emilee Roque, MW Powell Company
- Kimberly Wakefield, Knickerbocker Roofing & Paving
- Joseph Witek, Mortenson Roofing
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2015
- Alexandria DelSanto, Leak Stop Roofing
- Erin Dubin, Chicago Roofers JATC
- Jeff Swart, Mortenson Roofing
- Alxandra Wasko, Solaris Roofing
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2014
- Noel Cabanas, Pine Roofing Co.
- Vince Dietz, Dietz Vacuum
- Colleen Fahy, Combined Roofing
- Tom Jeffries, Clayton Roofing
- Andrew Mabry, All American Roofing
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