Key Games: 2020-01-20
 | vs |  |
| Middlesbroug | Final | Burnley U23 |
| 2 | 1 | |
| Turf Moor | ||
 |
Premier League Cup | |
 | vs |  |
| Plymouth U23 | Final | Watford U23 |
| 3 | 1 | |
| Stadium name not available | ||
 |
Premier League Cup | |
 | vs |  |
| Southampton | Postponed | Stoke City U |
| 0 | 0 | |
| bet365 Stadium | ||
 |
Premier League Cup | |
 | vs |  |
| Huddersfield | Final | Sunderland U |
| 1 | 2 | |
| Stadium name not available | ||
|
Premier League Cup | |
 | vs |  |
| Derby County | Postponed | Wolves U23 |
| 0 | 0 | |
| Stadium name not available | ||
 |
Premier League Cup | |
Headlines
| Mon, 20 Jan 2020 18:43:15 |
| Bradley to have surgery, likely sidelined about 4 months |
Source: |
| Mon, 20 Jan 2020 18:36:55 |
| Beckham's MLS team in Miami takes field for first time |
| Source: |
| Mon, 20 Jan 2020 16:53:10 |
| Real Madrid seals deal to sign Brazilian teen Reinier |
| Source: |
| Mon, 20 Jan 2020 15:34:58 |
| Prediction: Chelsea vs Arsenal |
Source: |
| Mon, 20 Jan 2020 15:22:37 |
| Ronaldo return to form helps Juventus rise to top again |
| Source: |
