Middlesbrough v Crewe Alexandra, 13 August 2019
| Score | 2-2 :: penalties 4-2 to Crewe Alexandra |
| Competition | League Cup 1st round |
| Venue | Riverside Stadium |
| Attendance | 7,897 |
View Middlesbrough v Crewe Alexandra head to head
Kick-off: 7.45pm
Crewe Alexandra won 4-2 on penalties