| Year | Name | League | Award |
| 2023 | George Springer | A.L. | Gold Gloves |
| 2023 | Rafael Devers | A.L. | League All-Star – Reserve |
| 2023 | Luis Rengifo | A.L. | League All-Star – Reserve |
| Year | Name | League | Award |
| 2022 | Whit Merrifield | A.L. | Gold Gloves |
| 2022 | Bryan Reynolds | A.L. | League All-Star – Reserve |
| 2022 | George Springer | A.L. | League All-Star – Reserve |
| 2022 | Rafael Devers | A.L. | League All-Star – Starter |
| Year | Name | League | Award |
| 2021 | Eloy Jimenez | A.L. | League All-Star – Reserve |
| 2021 | Sean Murphy | A.L. | League All-Star – Reserve |
| 2021 | Adam Plutko | A.L. | League All-Star – Reserve |
| 2021 | George Springer | A.L. | League All-Star – Reserve |
| 2021 | Tyler Webb | A.L. | League All-Star – Reserve |
| 2021 | Paul Roe | A.L. | All-Star Coaching Staff |
| Year | Name | League | Award |
| 2020 | Whit Merrifield | A.L. | Gold Gloves |
| 2020 | George Springer | A.L. | Gold Gloves |
| 2020 | Whit Merrifield | A.L. | League All-Star – Reserve |
| 2020 | Bryan Reynolds | A.L. | League All-Star – Reserve |
| 2020 | Bryan Reynolds | A.L. | Rookie of the Year |
| Year | Name | League | Award |
| 2019 | Anthony Rizzo | A.L. | Gold Gloves |
| 2019 | Carlos Santana | A.L. | League All-Star – Reserve |
| Year | Name | League | Award |
| 2018 | George Springer | A.L. | Gold Gloves |
| 2018 | Todd Helton | A.L. | Hall of Fame |
| 2018 | Anthony Rizzo | A.L. | League All-Star – Reserve |
| 2018 | Carlos Santana | A.L. | League All-Star – Reserve |
| 2018 | Jean Segura | A.L. | League All-Star – Reserve |
| 2018 | George Springer | A.L. | League All-Star – Reserve |
| 2018 | Felipe Vazquez | A.L. | League All-Star – Reserve |
| 2018 | Felipe Vazquez | A.L. | Rolaids Reliever of the Year |
| Year | Name | League | Award |
| 2017 | Jackie Bradley | A.L. | Gold Gloves |
| 2017 | Trevor Williams | A.L. | Gold Gloves |
| 2017 | Jim Thome | A.L. | Hall of Fame |
| 2017 | Jackie Bradley | A.L. | League All-Star – Reserve |
| 2017 | Anthony Rizzo | A.L. | League All-Star – Starter |
| 2017 | Jean Segura | A.L. | League All-Star – Starter |
| Year | Name | League | Award |
| 2016 | Anthony Rizzo | A.L. | Gold Gloves |
| 2016 | Jackie Bradley | A.L. | League All-Star – Reserve |
| 2016 | Anthony Rizzo | A.L. | League All-Star – Reserve |
| Year | Name | League | Award |
| 2015 | Anthony Rizzo | A.L. | League All-Star – Reserve |
| 2015 | Giancarlo Stanton | A.L. | League All-Star – Starter |
| Year | Name | League | Award |
| 2014 | Jean Segura | A.L. | Gold Gloves |
| 2014 | Michael Bourn | A.L. | League All-Star – Reserve |
| 2014 | Nick Markakis | A.L. | League All-Star – Reserve |
| 2014 | Max Scherzer | A.L. | League All-Star – Reserve |
| 2014 | Neil Walker | A.L. | League All-Star – Reserve |
| 2014 | Carlos Santana | A.L. | League All-Star – Starter |
| 2014 | Chris Archer | A.L. | Rookie of the Year |
| 2014 | Paul Roe | A.L. | All-Star Coaching Staff |
| Year | Name | League | Award |
| 2013 | Michael Bourn | A.L. | Gold Gloves |
| 2013 | James Loney | A.L. | Gold Gloves |
| 2013 | Michael Bourn | A.L. | League All-Star – Starter |
| 2013 | Giancarlo Stanton | A.L. | League All-Star – Starter |
| Year | Name | League | Award |
| 2012 | Aramis Ramirez | A.L. | League All-Star – Reserve |
| 2012 | Carlos Santana | A.L. | League All-Star – Reserve |
| Year | Name | League | Award |
| 2011 | Michael Bourn | A.L. | Gold Gloves |
| 2011 | Nick Markakis | A.L. | Gold Gloves |
| 2011 | Jamie Garcia | A.L. | League All-Star – Reserve |
| 2011 | Rafael Soriano | A.L. | League All-Star – Reserve |
| Year | Name | League | Award |
| 2010 | Michael Bourn | A.L. | Gold Gloves |
| 2010 | Jason Bartlett | A.L. | League All-Star – Reserve |
| 2010 | Trevor Cahill | A.L. | Rookie of the Year |
| Year | Name | League | Award |
| 2009 | Nick Markakis | A.L. | Gold Gloves |
| 2009 | Nick Markakis | A.L. | League All-Star – Reserve |
| Year | Name | League | Award |
| 2008 | Shaun Marcum | A.L. | League All-Star – Reserve |
| 2008 | Vladimir Guerrero | A.L. | League All-Star – Starter |
| Year | Name | League | Award |
| 2007 | Orlando Hudson | A.L. | Gold Gloves |
| 2007 | Vladimir Guerrero | A.L. | League All-Star – Reserve |
| Year | Name | League | Award |
| 2006 | Andy Pettitte | A.L. | Cy Young Award |
| 2006 | Todd Helton | A.L. | Gold Gloves |
| 2006 | Orlando Hudson | A.L. | Gold Gloves |
| 2006 | Bobby Abreu | A.L. | League All-Star – Starter |
| 2006 | Vladimir Guerrero | A.L. | League All-Star – Starter |
| 2006 | Todd Helton | A.L. | League All-Star – Starter |
| 2006 | Andy Pettitte | A.L. | League All-Star – Starter |
| 2006 | Aramis Ramirez | A.L. | League All-Star – Starter |
| 2006 | Vladimir Guerrero | A.L. | Most Valuable Player |
| 2006 | Paul Roe | A.L. | All-Star Coaching Staff |
| Year | Name | League | Award |
| 2005 | Todd Helton | A.L. | Gold Gloves |
| 2005 | Vladimir Guerrero | A.L. | League All-Star – Reserve |
| 2005 | Jim Thome | A.L. | League All-Star – Reserve |
| 2005 | Todd Helton | A.L. | League All-Star – Starter |
| Year | Name | League | Award |
| 2004 | Nomar Garciaparra | A.L. | League All-Star – Reserve |
| 2004 | Jim Thome | A.L. | League All-Star – Reserve |
| 2004 | Jose Guillen | A.L. | League All-Star – Starter |
| 2004 | Todd Helton | A.L. | League All-Star – Starter |
| 2004 | Paul Roe | A.L. | All-Star Coaching Staff |
| Year | Name | League | Award |
| 2003 | Todd Helton | A.L. | Gold Gloves |
| 2003 | Bobby Abreu | A.L. | League All-Star – Reserve |
| 2003 | Nomar Garciaparra | A.L. | League All-Star – Reserve |
| 2003 | Jim Thome | A.L. | League All-Star – Reserve |
| 2003 | Todd Helton | A.L. | League All-Star – Starter |
| 2003 | Jim Thome | A.L. | Most Valuable Player |
| 2003 | Paul Roe | A.L. | All-Star Coaching Staff |
| Year | Name | League | Award |
| 2002 | Todd Helton | A.L. | Gold Gloves |
| 2002 | Freddy Garcia | A.L. | League All-Star – Reserve |
| 2002 | Vladimir Guerrero | A.L. | League All-Star – Reserve |
| 2002 | Todd Helton | A.L. | League All-Star – Starter |
| 2002 | Todd Helton | A.L. | Most Valuable Player |
| 2002 | Paul Roe | A.L. | All-Star Coaching Staff |
| Year | Name | League | Award |
| 2001 | Mike Cameron | A.L. | Gold Gloves |
| 2001 | Bobby Abreu | A.L. | League All-Star – Reserve |
| 2001 | Vladimir Guerrero | A.L. | League All-Star – Reserve |
| 2001 | Todd Helton | A.L. | League All-Star – Reserve |
| 2001 | Nomar Garciaparra | A.L. | League All-Star – Starter |
| 2001 | Paul Roe | A.L. | Manager of the Year |
| Year | Name | League | Award |
| 2000 | Bobby Abreu | A.L. | League All-Star – Reserve |
| 2000 | Nomar Garciaparra | A.L. | League All-Star – Starter |
| Year | Name | League | Award |
| 1999 | Nomar Garciaparra | A.L. | League All-Star – Starter |
| 1999 | Vladimir Guerrero | A.L. | League All-Star – Starter |
| 1999 | Scott Spiezio | A.L. | League All-Star – Starter |
| 1999 | Todd Helton | A.L. | Rookie of the Year |
| Year | Name | League | Award |
| 1998 | Andy Pettitte | A.L. | League All-Star – Reserve |
| 1998 | Aaron Small | A.L. | League All-Star – Reserve |
| 1998 | Nomar Garciaparra | A.L. | League All-Star – Starter |
| 1998 | Nomar Garciaparra | A.L. | Rookie of the Year |
| 1998 | Paul Roe | A.L. | All-Star Coaching Staff |
| Year | Name | League | Award |
| 1997 | Brian Mcrae | A.L. | Gold Gloves |
| 1997 | Jim Thome | A.L. | League All-Star – Starter |