Sherpa Van Trophy 1988-89 
Winners: Bolton Wanderers Runners-up: Torquay United Winners from previous season: Wolverhampton Wanderers Preliminary round
| Northern section
| | Group 1 | | 29 November 1988 | Carlisle United | 1 | - | 1 | Scarborough | 1,437 | Brunton Park, Carlisle | | 6 December 1988 | Darlington | 3 | - | 2 | Carlisle United | 867 | Feethams, Darlington | | 14 December 1988 | Scarborough | 4 | - | 0 | Darlington | 1,257 | McCain Stadium, Scarborough | | Final Group 1 table | P | W | D | L | F | A | Pts | Goal Diff | | 1 | Scarborough | 2 | 1 | 1 | 0 | 5 | 1 | 4 | +4 | | 2 | Darlington | 2 | 1 | 0 | 1 | 3 | 6 | 3 | -3 | | 3 | Carlisle United | 2 | 0 | 1 | 1 | 3 | 4 | 1 | -1 |
| Group 2
| | 22 November 1988 | York City | 0 | - | 2 | Burnley | 1,648 | Bootham Crescent, York | | 29 November 1988 | Burnley | 3 | - | 0 | Hartlepool United | 3,478 | Turf Moor, Burnley | | 13 December 1988 | Hartlepool United | 0 | - | 2 | York City | 1,396 | Victoria Park, Hartlepool | | Final Group 2 table | P | W | D | L | F | A | Pts | Goal Diff | | 1 | Burnley | 2 | 2 | 0 | 0 | 5 | 0 | 6 | +5 | | 2 | York City | 2 | 1 | 0 | 1 | 2 | 2 | 3 | 0 | | 3 | Hartlepool United | 2 | 0 | 0 | 2 | 0 | 5 | 0 | -5 |
| Group 3
| | 22 November 1988 | Wigan Athletic | 1 | - | 2 | Blackpool | 1,217 | Springfield Park, Wigan | | 6 December 1988 | Blackpool | 2 | - | 0 | Rochdale | 2,128 | Bloomfield Road, Blackpool | | 13 December 1988 | Rochdale | 0 | - | 2 | Wigan Athletic | 1,134 | Spotland, Rochdale | | Final Group 3 table | P | W | D | L | F | A | Pts | Goal Diff | | 1 | Blackpool | 2 | 2 | 0 | 0 | 4 | 1 | 6 | +3 | | 2 | Wigan Athletic | 2 | 1 | 0 | 1 | 3 | 2 | 3 | +1 | | 3 | Rochdale | 2 | 0 | 0 | 2 | 0 | 4 | 0 | -4 |
| Group 4
| | 29 November 1988 | Grimsby Town | 1 | - | 0 | Rotherham United | 1,194 | Blundell Park, Cleethorpes | | 6 December 1988 | Doncaster Rovers | 1 | - | 1 | Grimsby Town | 681 | Belle Vue, Doncaster | | 13 December 1988 | Rotherham United | 2 | - | 1 | Doncaster Rovers | 1,790 | Millmoor, Rotherham | | Final Group 4 table | P | W | D | L | F | A | Pts | Goal Diff | | 1 | Grimsby Town | 2 | 1 | 1 | 0 | 2 | 1 | 4 | +1 | | 2 | Rotherham United | 2 | 1 | 0 | 1 | 2 | 2 | 3 | 0 | | 3 | Doncaster Rovers | 2 | 0 | 1 | 1 | 2 | 3 | 1 | -1 |
| Group 5
| | 6 December 1988 | Scunthorpe United | 1 | - | 2 | Halifax Town | 1,547 | Glanford Park, Scunthorpe | | 13 December 1988 | Huddersfield Town | 1 | - | 0 | Scunthorpe United | 2,216 | Leeds Road, Huddersfield | | 20 December 1988 | Halifax Town | 1 | - | 0 | Huddersfield Town | 2,437 | The Shay, Halifax | | Final Group 5 table | P | W | D | L | F | A | Pts | Goal Diff | | 1 | Halifax Town | 2 | 2 | 0 | 0 | 3 | 1 | 6 | +2 | | 2 | Huddersfield Town | 2 | 1 | 0 | 1 | 1 | 1 | 3 | 0 | | 3 | Scunthorpe United | 2 | 0 | 0 | 2 | 1 | 3 | 0 | -2 |
| Group 6
| | 6 December 1988 | Bolton Wanderers | 1 | - | 0 | Preston North End | 2,690 | Burnden Park, Bolton | | 13 December 1988 | Preston North End | 4 | - | 0 | Rochdale | 2,900 | Deepdale, Preston | | 20 December 1988 | Bury | 1 | - | 0 | Bolton Wanderers | 2,032 | Gigg Lane, Bury | | Final Group 6 table | P | W | D | L | F | A | Pts | Goal Diff | | 1 | Preston North End | 2 | 1 | 0 | 1 | 4 | 1 | 3 | +3 | | 2 | Bolton Wanderers | 2 | 1 | 0 | 1 | 1 | 1 | 3 | 0 | | 3 | Bury | 2 | 1 | 0 | 1 | 1 | 4 | 3 | -3 |
| Group 7
| | 28 November 1988 | Stockport County | 1 | - | 1 | Crewe Alexandra | 1,328 | Edgeley Park, Stockport | | 5 December 1988 | Tranmere Rovers | 2 | - | 1 | Stockport County | 1,494 | Prenton Park, Birkenhead | | 13 December 1988 | Crewe Alexandra | 1 | - | 1 | Tranmere Rovers | 1,460 | Gresty Road, Crewe | | Final Group 7 table | P | W | D | L | F | A | Pts | Goal Diff | | 1 | Tranmere Rovers | 2 | 1 | 1 | 0 | 3 | 2 | 4 | +1 | | 2 | Crewe Alexandra | 2 | 0 | 2 | 0 | 2 | 2 | 2 | 0 | | 3 | Stockport County | 2 | 0 | 1 | 1 | 2 | 3 | 1 | -1 |
| Group 8
| | 5 December 1988 | Wrexham | 1 | - | 1 | Sheffield United | 1,510 | Racecourse Ground, Wrexham | | 13 December 1988 | Sheffield United | 2 | - | 2 | Chester City | 2,981 | Bramall Lane, Sheffield | | 21 December 1988 | Chester City | 1 | - | 2 | Wrexham | 3,887 | Sealand Road, Chester | | Final Group 8 table | P | W | D | L | F | A | Pts | Goal Diff | | 1 | Wrexham | 2 | 2 | 0 | 0 | 3 | 2 | 6 | +1 | | 2 | Sheffield United | 2 | 1 | 0 | 1 | 3 | 3 | 3 | 0 | | 3 | Chester City | 2 | 0 | 0 | 2 | 3 | 4 | 0 | -1 |
| Southern Section
| Group 1 | | 22 November 1988 | Fulham | 0 | - | 2 | Brentford | 2,376 | Craven Cottage, London | | 29 November 1988 | Brentford | 2 | - | 0 | Gillingham | 3,713 | Griffin Park, London | | 10 December 1988 | Gillingham | 2 | - | 1 | Fulham | 1,970 | Priestfield, Gillingham | | Final Group 1 table | P | W | D | L | F | A | Pts | Goal Diff | | 1 | Brentford | 2 | 2 | 0 | 0 | 4 | 0 | 6 | +4 | | 2 | Gillingham | 2 | 1 | 0 | 1 | 2 | 3 | 3 | -1 | | 3 | Fulham | 2 | 0 | 0 | 2 | 1 | 4 | 0 | -3 |
| Group 2
| | 29 November 1988 | Mansfield Town | 1 | - | 1 | Notts County | 2,477 | Field Mill, Mansfield | | 6 December 1988 | Notts County | 1 | - | 1 | Chesterfield | 2,005 | Meadow Lane, Nottingham | | 10 December 1988 | Chesterfield | 2 | - | 1 | Mansfield Town | 2,640 | Recreation Ground, Chesterfield | | Final Group 2 table | P | W | D | L | F | A | Pts | Goal Diff | | 1 | Chesterfield | 2 | 1 | 1 | 0 | 3 | 2 | 4 | +1 | | 2 | Notts County | 2 | 0 | 2 | 0 | 2 | 2 | 2 | 0 | | 3 | Mansfield Town | 2 | 0 | 1 | 1 | 2 | 3 | 1 | -1 |
| Group 3
| | 22 November 1988 | Southend United | 2 | - | 1 | Lincoln City | 1,176 | Roots Hall, Southend-on-Sea | 30 November 1988 | Lincoln City | 1 | - | 2 | Colchester United | 1,448 | Sincil Bank, Lincoln | | 20 December 1988 | Colchester United | 2 | - | 1 | Southend United | 993 | Layer Road, Colchester | | Final Group 3 table | P | W | D | L | F | A | Pts | Goal Diff | | 1 | Colchester United | 2 | 2 | 0 | 0 | 4 | 2 | 6 | +2 | | 2 | Southend United | 2 | 1 | 0 | 1 | 3 | 3 | 3 | 0 | | 3 | Lincoln City | 2 | 0 | 0 | 2 | 2 | 4 | 0 | -2 |
| Group 4 | | 23 November 1988 | Bristol Rovers | 1 | - | 0 | Bristol City | 3,940 | Twerton Park, Bath | | 6 December 1988 | Bristol City | 2 | - | 0 | Exeter City | 3,642 | Ashton Gate, Bristol | | 14 December 1988 | Exeter City | 1 | - | 1 | Bristol Rovers | 1,609 | St James's Park, Exeter | | Final Group 4 table | P | W | D | L | F | A | Pts | Goal Diff | | 1 | Bristol Rovers | 2 | 1 | 1 | 0 | 2 | 1 | 4 | +1 | | 2 | Bristol City | 2 | 1 | 0 | 1 | 2 | 1 | 3 | +1 | | 3 | Exeter City | 2 | 0 | 1 | 1 | 1 | 3 | 1 | -2 |
| Group 5 | | 29 November 1988 | Swansea City | 1 | - | 0 | Torquay United | 1,409 | Vetch Field, Swansea | | 6 December 1988 | Cardiff City | 2 | - | 0 | Swansea City | 2,986 | Ninian Park, Cardiff | | 20 December 1988 | Torquay United | 3 | - | 1 | Cardiff City | 1,187 | Plainmoor, Torquay | | Final Group 5 table | P | W | D | L | F | A | Pts | Goal Diff | | 1 | Torquay United | 2 | 1 | 0 | 1 | 3 | 2 | 3 | +1 | | 2 | Cardiff City | 2 | 1 | 0 | 1 | 3 | 3 | 3 | 0 | | 3 | Swansea City | 2 | 1 | 0 | 1 | 1 | 2 | 3 | -1 |
| Group 6
| | 21 November 1988 | Port Vale | 1 | - | 1 | Hereford United | 1,843 | Vale Park, Burslem | | 30 November 1988 | Hereford United | 2 | - | 2 | Wolverhampton Wanderers | 4,215 | Edgar Street, Hereford | | 13 December 1988 | Wolverhampton Wanderers | 5 | - | 1 | Port Vale | 9,734 | Molineux, Wolverhampton | | Final Group 6 table | P | W | D | L | F | A | Pts | Goal Diff | | 1 | Wolverhampton Wanderers | 2 | 1 | 1 | 0 | 7 | 3 | 4 | +4 | | 2 | Hereford United | 2 | 0 | 2 | 0 | 3 | 3 | 2 | 0 | | 3 | Port Vale | 2 | 0 | 1 | 1 | 2 | 6 | 1 | -4 |
| Group 7
| | 30 November 1988 | Reading | 5 | - | 2 | Aldershot | 2,837 | Elm Park, Reading | | 6 December 1988 | Leyton Orient | 1 | - | 1 | Reading | 1,174 | Brisbane Road, London | | 10 January 1989 | Aldershot | 1 | - | 3 | Leyton Orient | 1,310 | Recreation Ground, Aldershot | | Final Group 7 table | P | W | D | L | F | A | Pts | Goal Diff | | 1 | Reading | 2 | 1 | 1 | 0 | 6 | 3 | 4 | +3 | | 2 | Leyton Orient | 2 | 1 | 1 | 0 | 4 | 2 | 4 | +2 | | 3 | Aldershot | 2 | 0 | 0 | 2 | 3 | 8 | 0 | -5 |
| Group 8
| | 22 November 1988 | Northampton Town | 1 | - | 1 | Cambridge United | 1,806 | County Ground, Northampton | | 29 November 1988 | Cambridge United | 2 | - | 2 | Peterborough United | 1,296 | Abbey Stadium, Cambridge | | 21 December 1988 | Peterborough United | 0 | - | 2 | Northampton Town | 1,754 | London Road, Peterborough | | Final Group 8 table | P | W | D | L | F | A | Pts | Goal Diff | | 1 | Northampton Town | 2 | 1 | 1 | 0 | 3 | 1 | 4 | +2 | | 2 | Cambridge United | 2 | 0 | 2 | 0 | 3 | 3 | 2 | 0 | | 3 | Peterborough United | 2 | 0 | 1 | 1 | 2 | 4 | 1 | -2 |
| First round | Northern section | | 7 January 1989 | Scarborough | 3 | - | 1 | York City | 2,779 | McCain Stadium, Scarborough | | 17 January 1989 | Blackpool | 4 | - | 3 | Rotherham United | 1,620 | Bloomfield Park, Blackpool | | 17 January 1989 | Burnley | 1 | - | 1 | Crewe Alexandra (won 2-4 on pens.) | 6,392 | Turf Moor, Burnley (aet) | | 17 January 1989 | Grimsby Town | 1 | - | 3 | Huddersfield Town | 2,116 | Blundell Park, Cleethorpes | | 17 January 1989 | Halifax Town | 3 | - | 0 | Darlington | 1,421 | The Shay, Halifax | | 17 January 1989 | Preston North End | 0 | - | 1 | Bolton Wanderers | 5,569 | Deepdale, Preston | | 17 January 1989 | Tranmere Rovers | 0 | - | 1 | Wigan Athletic | 2,915 | Prenton Park, Birkenhead | | 17 January 1989 | Wrexham | 2 | - | 1 | Sheffield United | 2,653 | Racecourse Ground, Wrexham | Southern section | | 17 January 1989 | Brentford | 2 | - | 0 | Notts County | 3,194 | Griffin Park, London | | 17 January 1989 | Chesterfield | 4 | - | 2 | Cambridge United | 2,726 | Recreation Ground, Chesterfield | | 17 January 1989 | Colchester United | 3 | - | 1 | Leyton Orient | 1,736 | Layer Road, Colchester | | 17 January 1989 | Northampton Town | 2 | - | 1 | Southend United | 2,539 | County Ground, Northampton | | 17 January 1989 | Torquay United | 3 | - | 0 | Gillingham | 1,844 | Plainmoor, Torquay | | 18 January 1989 | Reading | 2 | - | 3 | Hereford United | 2,175 | Elm Park, Reading | | 24 January 1989 | Bristol Rovers | 2 | - | 1 | Cardiff City | 4,029 | Twerton Park, Bath | | 24 January 1989 | Wolverhampton Wanderers | 3 | - | 0 | Bristol City | 14,216 | Molineux, Wolverhampton | | Quarter-finals | | Northern section | | 21 February 1989 | Bolton Wanderers | 3 | - | 1 | Wrexham | 3,833 | Burnden Park, Bolton | | 21 February 1989 | Halifax Town | 0 | - | 2 | Blackpool | 3,281 | The Shay, Halifax | | 21 February 1989 | Huddersfield Town | 1 | - | 2 | Scarborough | 4,665 | Leeds Road, Huddersfield | | 21 February 1989 | Wigan Athletic | 0 | - | 1 | Crewe Alexandra | 3,004 | Springfield Park, Wigan | Southern section | | 14 February 1989 | Colchester United | 0 | - | 1 | Hereford United | 2,059 | Layer Road, Colchester | | 21 February 1989 | Chesterfield | 0 | - | 1 | Brentford | 4,207 | Recreation Ground, Chesterfield | | 21 February 1989 | Wolverhampton Wanderers | 3 | - | 1 | Northampton Town | 16,815 | Molineux, Wolverhampton | | 22 February 1989 | Bristol Rovers | 0 | - | 1 | Torquay United | 4,316 | Twerton Park, Bath | Semi-Finals | Northern section | | 21 March 1989 | Blackpool | 1 | - | 0 | Scarborough | 4,300 | Bloomfield Road, Blackpool | | 21 March 1989 | Crewe Alexandra | 1 | - | 2 | Bolton Wanderers | 5,928 | Gresty Road, Crewe | Southern section | | 21 March 1989 | Brentford | 0 | - | 1 | Torquay United | 5,802 | Griffin Park, London | | 22 March 1989 | Hereford United | 0 | - | 2 | Wolverhampton Wanderers | 10,204 | Edgar Street, Hereford | Area Finals | Northern section: 1st leg | | 11 April 1989 | Bolton Wanderers | 1 | - | 0 | Blackpool | 10,345 | Burnden Park, Bolton | | Southern section: 1st leg | | 12 April 1989 | Torquay United | 1 | - | 2 | Wolverhampton Wanderers | 4,612 | Plainmoor, Torquay | | Northern section: 2nd leg | | 18 April 1989 | Blackpool | 1 | - | 1 | Bolton Wanderers | 9,027 | Bloomfield Road, Blackpool | | (Bolton Wanderers win 2-1 on aggregate) | Southern section: 2nd leg | | 18 April 1989 | Wolverhampton Wanderers | 0 | - | 2 | Torquay United | 22,532 | Molineux, Wolverhampton | (Toruqay United win 3-2 on aggregate) | National final | | 28 May 1989 | Bolton Wanderers | 4 | - | 1 | Torquay United | 46,513 | Wembley Stadium, London |
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