| 23 Aug 58 | r00  | MiddlesbroughMiddlesbrough | 9 - 0 | BrightonBrighton |
| 25 Aug 58 | r00 | Sheffield UnitedSheffield Uni | 0 - 1 | MiddlesbroughMiddlesbrough |
| 30 Aug 58 | r00 | GrimsbyGrimsby | 3 - 2 | MiddlesbroughMiddlesbrough |
| 03 Sep 58 | r00 | MiddlesbroughMiddlesbrough | 0 - 0 | Sheffield UnitedSheffield Uni |
| 06 Sep 58 | r00 | MiddlesbroughMiddlesbrough | 2 - 1 | LiverpoolLiverpool |
| 11 Sep 58 | r00 | RotherhamRotherham | 1 - 4 | MiddlesbroughMiddlesbrough |
| 13 Sep 58 | r00 | StokeStoke | 3 - 1 | MiddlesbroughMiddlesbrough |
| 17 Sep 58 | r00 | MiddlesbroughMiddlesbrough | 1 - 2 | RotherhamRotherham |
| 20 Sep 58 | r00 | CharltonCharlton | 1 - 0 | MiddlesbroughMiddlesbrough |
| 27 Sep 58 | r00 | MiddlesbroughMiddlesbrough | 0 - 0 | Bristol CityBristol City |
| 04 Oct 58 | r00 | CardiffCardiff | 3 - 2 | MiddlesbroughMiddlesbrough |
| 11 Oct 58 | r00 | MiddlesbroughMiddlesbrough | 0 - 0 | SunderlandSunderland |
| 18 Oct 58 | r00 | LincolnLincoln | 1 - 1 | MiddlesbroughMiddlesbrough |
| 25 Oct 58 | r00 | MiddlesbroughMiddlesbrough | 2 - 3 | FulhamFulham |
| 01 Nov 58 | r00 | SwanseaSwansea | 5 - 2 | MiddlesbroughMiddlesbrough |
| 08 Nov 58 | r00 | MiddlesbroughMiddlesbrough | 6 - 1 | ScunthorpeScunthorpe |
| 15 Nov 58 | r00 | Leyton OrientLeyton Orient | 5 - 2 | MiddlesbroughMiddlesbrough |
| 22 Nov 58 | r00 | MiddlesbroughMiddlesbrough | 5 - 0 | DerbyDerby |
| 29 Nov 58 | r00 | Bristol RoversBristol Rover | 3 - 1 | MiddlesbroughMiddlesbrough |
| 06 Dec 58 | r00 | MiddlesbroughMiddlesbrough | 2 - 3 | IpswichIpswich |
| 13 Dec 58 | r00 | Sheffield WedsSheffield Wed | 2 - 0 | MiddlesbroughMiddlesbrough |
| 20 Dec 58 | r00 | BrightonBrighton | 4 - 6 | MiddlesbroughMiddlesbrough |
| 26 Dec 58 | r00 | MiddlesbroughMiddlesbrough | 3 - 1 | BarnsleyBarnsley |
| 27 Dec 58 | r00 | BarnsleyBarnsley | 1 - 0 | MiddlesbroughMiddlesbrough |
| 01 Jan 59 | r00 | MiddlesbroughMiddlesbrough | 3 - 1 | Huddersfield TownHuddersfield |
| 31 Jan 59 | r00 | MiddlesbroughMiddlesbrough | 0 - 0 | StokeStoke |
| 07 Feb 59 | r00 | MiddlesbroughMiddlesbrough | 1 - 3 | CharltonCharlton |
| 14 Feb 59 | r00 | Bristol CityBristol City | 2 - 2 | MiddlesbroughMiddlesbrough |
| 21 Feb 59 | r00 | MiddlesbroughMiddlesbrough | 1 - 1 | CardiffCardiff |
| 28 Feb 59 | r00 | ScunthorpeScunthorpe | 0 - 3 | MiddlesbroughMiddlesbrough |
| 07 Mar 59 | r00 | MiddlesbroughMiddlesbrough | 1 - 2 | LincolnLincoln |
| 11 Mar 59 | r00 | MiddlesbroughMiddlesbrough | 1 - 0 | GrimsbyGrimsby |
| 14 Mar 59 | r00 | FulhamFulham | 3 - 2 | MiddlesbroughMiddlesbrough |
| 21 Mar 59 | r00 | MiddlesbroughMiddlesbrough | 6 - 2 | SwanseaSwansea |
| 28 Mar 59 | r00 | SunderlandSunderland | 0 - 0 | MiddlesbroughMiddlesbrough |
| 30 Mar 59 | r00 | Huddersfield TownHuddersfield | 5 - 1 | MiddlesbroughMiddlesbrough |
| 04 Apr 59 | r00 | MiddlesbroughMiddlesbrough | 4 - 2 | Leyton OrientLeyton Orient |
| 08 Apr 59 | r00 | LiverpoolLiverpool | 1 - 2 | MiddlesbroughMiddlesbrough |
| 11 Apr 59 | r00 | DerbyDerby | 0 - 3 | MiddlesbroughMiddlesbrough |
| 18 Apr 59 | r00 | MiddlesbroughMiddlesbrough | 2 - 2 | Bristol RoversBristol Rover |
| 22 Apr 59 | r00 | MiddlesbroughMiddlesbrough | 2 - 2 | Sheffield WedsSheffield Wed |
| 25 Apr 59 | r00 | IpswichIpswich | 2 - 1 | MiddlesbroughMiddlesbrough |
Team 1958-1959 Schedules
Birmingham City
Blackburn Rovers
Bolton Wanderers
Bristol City
Burnley
Cardiff City
Charlton Athletic
Derby County
Lincoln City
Middlesbrough
Millwall
Norwich City
Portsmouth
Preston North End
Queens Park Rangers
Sheffield United
Southampton
Stoke City
Swansea City
Watford
West Bromwich Albion
West Ham United
Wolverhampton Wanderers
Wrexham
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