After the September race at Indianapolis Motor Speedway, the 2019 Playoff field is set for the Monster Energy NASCAR Cup Series. Below is the schedule for the playoff season with the winner posted after each event.
Monster Energy NASCAR Cup Series Schedule
| Date | Track | Wins/Winner |
| Round of 16 Drivers | Kyle Busch Denny Hamlin Martin Truex Jr Kevin Harvick Joey Logano Brad Keselowski Chase Elliott Kurt Busch* Alex Bowman Erik Jones* Kyle Larson Ryan Blaney William Byron Aric Almirola* Clint Bowyer Ryan Newman* * Bold=Drivers eliminated this Round | 4 4 4 3 2 3 2 1 1 1 0 0 0 0 0 0 – |
| Sunday, September 15th | Las Vegas Motor Speedway Results (Round of 16 Begins) | Martin Truex Jr Joe Gibbs Racing |
| Saturday, September 21st | Richmond Raceway Results | Martin Truex Jr Joe Gibbs Racing |
| Sunday, September 29th | Charlotte Roval Results (Top-12 Move on to Round of 12) | Chase Elliott Hendrick Motorsports |
| Round of 12 Drivers | Kyle Busch Martin Truex Jr Denny Hamlin Joey Logano Kevin Harvick Chase Elliott Brad Keselowski* Kyle Larson Alex Bowman* Ryan Blaney William Byron* Clint Bowyer* * Bold=Drivers eliminated this Round | 4 6 4 2 3 3 3 0 1 0 0 0 – |
| Sunday, October 6th | Dover International Speedway Results (Round of 12 Begins) | Kyle Larson Chip Ganassi Racing |
| Sunday, October 13th | Talladega Superspeedway Results | Ryan Blaney Team Penske |
| Sunday, October 20th | Kansas Speedway Results (Top-Eight Move on to Round of 8) | Denny Hamlin Joe Gibbs Racing |
| Round of 8 Drivers | Kyle Busch Martin Truex Jr. Denny Hamlin Joey Logano* Kevin Harvick Chase Elliott* Kyle Larson* Ryan Blaney* * Bold=Drivers eliminated this Round | 4 6 5 2 3 3 1 1 – |
| Sunday, October 27th | Martinsville Speedway Results (Round of 8 Begins) | Martin Truex Jr Joe Gibbs Racing |
| Sunday, November 3rd | Texas Motor Speedway Results | Kevin Harvick Stewart-Haas Racing |
| Sunday, November 10th | ISM Raceway Phoenix Results (Top-Four Move on to Championship Round) | Denny Hamlin Joe Gibbs Racing |
| Championship 4 Drivers | Martin Truex Jr Denny Hamlin Kevin Harvick Kyle Busch | 7 6 4 4 |
| Sunday, November 17th | Homestead-Miami Speedway (Final Four Championship Round) |