| 10 Aug 68 | r00  | MiddlesbroughMiddlesbrough | 2 - 1 | PrestonPreston |
| 14 Aug 68 | r00 | NorwichNorwich | 0 - 2 | MiddlesbroughMiddlesbrough |
| 17 Aug 68 | r00 | PortsmouthPortsmouth | 3 - 0 | MiddlesbroughMiddlesbrough |
| 20 Aug 68 | r00 | MiddlesbroughMiddlesbrough | 4 - 0 | Crystal PalaceCrystal Palac |
| 24 Aug 68 | r00 | MiddlesbroughMiddlesbrough | 1 - 0 | CarlisleCarlisle |
| 27 Aug 68 | r00 | MiddlesbroughMiddlesbrough | 1 - 1 | Huddersfield TownHuddersfield |
| 31 Aug 68 | r00 | HullHull | 3 - 0 | MiddlesbroughMiddlesbrough |
| 07 Sep 68 | r00 | CardiffCardiff | 2 - 0 | MiddlesbroughMiddlesbrough |
| 14 Sep 68 | r00 | MiddlesbroughMiddlesbrough | 3 - 1 | BirminghamBirmingham |
| 21 Sep 68 | r00 | BuryBury | 2 - 3 | MiddlesbroughMiddlesbrough |
| 28 Sep 68 | r00 | MiddlesbroughMiddlesbrough | 1 - 0 | CharltonCharlton |
| 05 Oct 68 | r00 | MiddlesbroughMiddlesbrough | 0 - 0 | DerbyDerby |
| 08 Oct 68 | r00 | Huddersfield TownHuddersfield | 3 - 0 | MiddlesbroughMiddlesbrough |
| 12 Oct 68 | r00 | Sheffield UnitedSheffield Uni | 1 - 3 | MiddlesbroughMiddlesbrough |
| 19 Oct 68 | r00 | MiddlesbroughMiddlesbrough | 2 - 0 | FulhamFulham |
| 26 Oct 68 | r00 | Oxford UtdOxford Utd | 2 - 4 | MiddlesbroughMiddlesbrough |
| 09 Nov 68 | r00 | MillwallMillwall | 2 - 0 | MiddlesbroughMiddlesbrough |
| 16 Nov 68 | r00 | MiddlesbroughMiddlesbrough | 0 - 0 | BoltonBolton |
| 23 Nov 68 | r00 | Aston VillaAston Villa | 1 - 0 | MiddlesbroughMiddlesbrough |
| 30 Nov 68 | r00 | MiddlesbroughMiddlesbrough | 2 - 0 | BlackburnBlackburn |
| 03 Dec 68 | r00 | MiddlesbroughMiddlesbrough | 4 - 1 | Bristol CityBristol City |
| 07 Dec 68 | r00 | BlackpoolBlackpool | 1 - 1 | MiddlesbroughMiddlesbrough |
| 21 Dec 68 | r00 | FulhamFulham | 0 - 3 | MiddlesbroughMiddlesbrough |
| 26 Dec 68 | r00 | DerbyDerby | 3 - 2 | MiddlesbroughMiddlesbrough |
| 11 Jan 69 | r00 | Bristol CityBristol City | 3 - 0 | MiddlesbroughMiddlesbrough |
| 18 Jan 69 | r00 | MiddlesbroughMiddlesbrough | 1 - 1 | MillwallMillwall |
| 24 Jan 69 | r00 | MiddlesbroughMiddlesbrough | 2 - 0 | Oxford UtdOxford Utd |
| 28 Jan 69 | r00 | MiddlesbroughMiddlesbrough | 3 - 1 | Sheffield UnitedSheffield Uni |
| 01 Feb 69 | r00 | BoltonBolton | 0 - 0 | MiddlesbroughMiddlesbrough |
| 22 Feb 69 | r00 | MiddlesbroughMiddlesbrough | 2 - 1 | BlackpoolBlackpool |
| 01 Mar 69 | r00 | PrestonPreston | 1 - 2 | MiddlesbroughMiddlesbrough |
| 04 Mar 69 | r00 | MiddlesbroughMiddlesbrough | 0 - 0 | Aston VillaAston Villa |
| 08 Mar 69 | r00 | MiddlesbroughMiddlesbrough | 1 - 0 | PortsmouthPortsmouth |
| 15 Mar 69 | r00 | CarlisleCarlisle | 3 - 0 | MiddlesbroughMiddlesbrough |
| 22 Mar 69 | r00 | MiddlesbroughMiddlesbrough | 5 - 3 | HullHull |
| 25 Mar 69 | r00 | BlackburnBlackburn | 1 - 1 | MiddlesbroughMiddlesbrough |
| 29 Mar 69 | r00 | MiddlesbroughMiddlesbrough | 0 - 0 | CardiffCardiff |
| 04 Apr 69 | r00 | Crystal PalaceCrystal Palac | 0 - 0 | MiddlesbroughMiddlesbrough |
| 05 Apr 69 | r00 | CharltonCharlton | 2 - 0 | MiddlesbroughMiddlesbrough |
| 08 Apr 69 | r00 | MiddlesbroughMiddlesbrough | 0 - 0 | NorwichNorwich |
| 12 Apr 69 | r00 | MiddlesbroughMiddlesbrough | 2 - 3 | BuryBury |
| 19 Apr 69 | r00 | BirminghamBirmingham | 3 - 1 | MiddlesbroughMiddlesbrough |
Team 1968-1969 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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