| 1 | Sat 23 Mar 2019 | 1-0 v GibraltarGibraltar 0-1 Republic of Ireland | European Championship Qualification Group D |
| 2 | Tue 26 Mar 2019 | 231-0 v GeorgiaRepublic of Ireland 1-0 Georgia | European Championship Qualification Group D |
| 3 | Fri 7 Jun 2019 | 1-1 v DenmarkDenmark 1-1 Republic of Ireland | European Championship Qualification Group D |
| 4 | Mon 10 Jun 2019 | 2-0 v GibraltarRepublic of Ireland 2-0 Gibraltar | European Championship Qualification Group D |
| 5 | Fri 2 Aug 2019 | 233-3 v Luton TownLuton Town 3-3 Middlesbrough | Sky Bet Championship |
| 6 | Sat 10 Aug 2019 | 230-1 v BrentfordMiddlesbrough 0-1 Brentford | Sky Bet Championship |
| 7 | Sat 17 Aug 2019 | 230-1 v Blackburn RoversBlackburn Rovers 1-0 Middlesbrough | Sky Bet Championship |
| 8 | Tue 20 Aug 2019 | 231-0 v Wigan AthleticMiddlesbrough 1-0 Wigan Athletic | Sky Bet Championship |
| 9 | Sat 24 Aug 2019 | 231-1 v MillwallMiddlesbrough 1-1 Millwall | Sky Bet Championship |
| 10 | Sat 31 Aug 2019 | 232-2 v Bristol CityBristol City 2-2 Middlesbrough | Sky Bet Championship |
| 11 | Thu 5 Sep 2019 | 1-1 v SwitzerlandRepublic of Ireland 1-1 Switzerland | European Championship Qualification Group D |
| 12 | Sat 14 Sep 2019 | 231-0 v ReadingMiddlesbrough 1-0 Reading | Sky Bet Championship |
| 13 | Sat 21 Sep 2019 | 230-1 v Cardiff CityCardiff City 1-0 Middlesbrough | Sky Bet Championship |
| 14 | Sat 28 Sep 2019 | 231-4 v Sheffield WednesdayMiddlesbrough 1-4 Sheffield Wednesday | Sky Bet Championship |
| 15 | Tue 1 Oct 2019 | 231-1 v Preston North EndMiddlesbrough 1-1 Preston North End | Sky Bet Championship |
| 16 | Fri 4 Oct 2019 | 231-2 v Birmingham CityBirmingham City 2-1 Middlesbrough | Sky Bet Championship |
| 17 | Sat 12 Oct 2019 | 0-0 v GeorgiaGeorgia 0-0 Republic of Ireland | European Championship Qualification Group D |
| 18 | Tue 15 Oct 2019 | 0-2 v SwitzerlandSwitzerland 2-0 Republic of Ireland | European Championship Qualification Group D |
| 19 | Sat 19 Oct 2019 | 230-1 v West Bromwich AlbionMiddlesbrough 0-1 West Bromwich Albion | Sky Bet Championship |
| 20 | Sat 9 Nov 2019 | 23 2-2 v Queens Park RangersQueens Park Rangers 2-2 Middlesbrough | Sky Bet Championship |
| 21 | Mon 18 Nov 2019 | 1-1 v DenmarkRepublic of Ireland 1-1 Denmark | European Championship Qualification Group D |
| 22 | Sun 24 Nov 2019 | 232-2 v Hull CityMiddlesbrough 2-2 Hull City | Sky Bet Championship |
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