Saturday 15 August
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 15h00 |   Middlesbrough vs Lincoln | 2 - 1 | Championship Stage : MD1 | Riverside Stadium |
Saturday 22 August
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 15h00 |  Blackburn vs Middlesbrough | 2 - 1 | Championship Stage : MD2 | Ewood Park |
Saturday 29 August
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 12h30 |  Middlesbrough vs West Brom | 3 - 1 | Championship Stage : MD3 | Riverside Stadium |
Wednesday 2 September
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 20h00 |  Burnley vs Middlesbrough | 1 - 1 | Championship Stage : MD4 | Turf Moor |
Saturday 5 September
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 15h00 |  QPR vs Middlesbrough | - | Championship Stage : MD5 | Loftus Road |
Saturday 12 September
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 15h00 |  Middlesbrough vs Norwich | - | Championship Stage : MD7 | Riverside Stadium |
Tuesday 15 September
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 19h45 |  Middlesbrough vs Millwall | - | Championship Stage : MD6 | Riverside Stadium |
Saturday 19 September
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 15h00 |  Birmingham vs Middlesbrough | - | Championship Stage : MD8 | - |
Saturday 10 October
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 15h00 |  Middlesbrough vs Wolves | - | Championship Stage : MD9 | Riverside Stadium |
Tuesday 13 October
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 20h00 |  Stoke City vs Middlesbrough | - | Championship Stage : MD10 | Bet365 Stadium |
Saturday 17 October
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 12h30 |  Middlesbrough vs Cardiff | - | Championship Stage : MD11 | Riverside Stadium |
Friday 23 October
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 20h00 |  Bolton vs Middlesbrough | - | Championship Stage : MD12 | Toughsheet Community Stadium |
Saturday 31 October
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 16h00 |  Middlesbrough vs Charlton | - | Championship Stage : MD13 | Riverside Stadium |
Wednesday 4 November
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 20h45 |  Wrexham vs Middlesbrough | - | Championship Stage : MD14 | Racecourse Ground |
Saturday 7 November
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 16h00 |  Watford vs Middlesbrough | - | Championship Stage : MD15 | Vicarage Road |
Saturday 21 November
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 16h00 |  Middlesbrough vs Bristol City | - | Championship Stage : MD16 | Riverside Stadium |
Tuesday 24 November
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 20h45 |  Middlesbrough vs Swansea | - | Championship Stage : MD17 | Riverside Stadium |
Friday 27 November
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 21h00 |  Southampton vs Middlesbrough | - | Championship Stage : MD18 | - |
Saturday 5 December
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 13h30 |  Middlesbrough vs Derby | - | Championship Stage : MD19 | Riverside Stadium |
Tuesday 8 December
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 21h00 |  West Ham vs Middlesbrough | - | Championship Stage : MD20 | London Stadium |
Saturday 12 December
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 13h30 |  Preston vs Middlesbrough | - | Championship Stage : MD21 | Deepdale |
Saturday 19 December
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 16h00 |  Middlesbrough vs Portsmouth | - | Championship Stage : MD22 | Riverside Stadium |
Saturday 26 December
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 13h30 |  Sheffield Utd vs Middlesbrough | - | Championship Stage : MD23 | Bramall Lane |
Tuesday 29 December
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 20h45 | Middlesbrough vs Bolton | - | Championship Stage : MD24 | Riverside Stadium |
Friday 1 January
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 16h00 | Middlesbrough vs Preston | - | Championship Stage : MD25 | Riverside Stadium |
Saturday 16 January
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 16h00 | Cardiff vs Middlesbrough | - | Championship Stage : MD26 | Cardiff City Stadium |
Saturday 23 January
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 16h00 | Charlton vs Middlesbrough | - | Championship Stage : MD27 | The Valley |
Wednesday 27 January
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 20h45 | Middlesbrough vs Wrexham | - | Championship Stage : MD28 | Riverside Stadium |
Saturday 30 January
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 16h00 | Middlesbrough vs Watford | - | Championship Stage : MD29 | Riverside Stadium |
Saturday 6 February
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 16h00 | Bristol City vs Middlesbrough | - | Championship Stage : MD30 | Ashton Gate Stadium |
Saturday 13 February
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 16h00 | Norwich vs Middlesbrough | - | Championship Stage : MD31 | Carrow Road |
Wednesday 17 February
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 20h45 | Middlesbrough vs Stoke City | - | Championship Stage : MD32 | Riverside Stadium |
Saturday 20 February
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 16h00 | Middlesbrough vs Birmingham | - | Championship Stage : MD33 | Riverside Stadium |
Saturday 27 February
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 16h00 | Wolves vs Middlesbrough | - | Championship Stage : MD34 | Molineux Stadium |
Tuesday 2 March
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 20h45 | Middlesbrough vs Blackburn | - | Championship Stage : MD35 | Riverside Stadium |
Saturday 6 March
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 16h00 | Lincoln vs Middlesbrough | - | Championship Stage : MD36 | LNER Stadium |
Saturday 13 March
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 16h00 | Middlesbrough vs Southampton | - | Championship Stage : MD37 | Riverside Stadium |
Tuesday 16 March
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 20h45 | Derby vs Middlesbrough | - | Championship Stage : MD38 | Pride Park |
Saturday 20 March
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 16h00 | Middlesbrough vs Sheffield Utd | - | Championship Stage : MD39 | Riverside Stadium |
Saturday 3 April
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 15h00 | Portsmouth vs Middlesbrough | - | Championship Stage : MD40 | Fratton Park |
Tuesday 6 April
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 19h45 | Millwall vs Middlesbrough | - | Championship Stage : MD41 | The Den |
Saturday 10 April
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 15h00 | Middlesbrough vs QPR | - | Championship Stage : MD42 | Riverside Stadium |
Saturday 17 April
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 15h00 | West Brom vs Middlesbrough | - | Championship Stage : MD43 | The Hawthorns |
Tuesday 20 April
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 19h45 | Middlesbrough vs Burnley | - | Championship Stage : MD44 | Riverside Stadium |
Saturday 24 April
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 15h00 | Middlesbrough vs West Ham | - | Championship Stage : MD45 | Riverside Stadium |
Saturday 1 May
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 12h30 | Swansea vs Middlesbrough | - | Championship Stage : MD46 | Swansea.com Stadium |