| July |
| W | Mon 16/7/2007 | Frdly | Hutton Cranswick Unknown |  | 1-3 |  | Pickering Town Steve Baxter Mark Swales Mark Barber | HT: 0-0 |
| W | Wed 25/7/2007 | Frdly | Pickering Town Mark Swales 45pen Rob Eeles 75 Mark Barber 85 |  | 3-1 |  | Sheffield United Jordan Eagers 2 | Att: 230 HT: 1-1 |
| W | Sat 28/7/2007 | Frdly | Stokesley |  | 2-6 |  | Pickering Town Mark Swales (3) Ricky Greening Dan Boneham Mark Barber | |
| August |
| W | Wed 1/8/2007 | Frdly | Pickering Town Chris Batchelor 4 Mark Swales 12, 64 Dan Boneham 72 Liam Salt 78 |  | 5-0 |  | Whitby Town | Att: 120 HT: 2-0 |
| D | Sat 11/8/2007 | NCELP | Winterton Rangers |  | 0-0 |  | Pickering Town | Att: 75 |
| D | Tue 14/8/2007 | NCELP | Nostell Miners Welfare Ben Gilbert 1 |  | 1-1 |  | Pickering Town Joe Connor 90pen | Att: 80 HT: 1-0 |
| W | Sat 18/8/2007 | FACEP | Washington Glen Reay 86 |  | 1-3 |  | Pickering Town Steve Baxter 46, 53 Mark Swales 62pen | Att: 74 HT: 0-0 |
| L | Sat 25/8/2007 | NCELP | Liversedge Joe Hewitt 39 Luke Sherman 47 Paul Smith 86 |  | 3-0 |  | Pickering Town | Att: 102 HT: 1-0 |
| L | Mon 27/8/2007 | NCELP | Lincoln Moorlands Railway Matthew Roche 44 Adam Gilbert 57 Jamie Stokes 65 |  | 3-0 |  | Pickering Town | Att: 57 HT: 1-0 |
| September |
| L | Sat 1/9/2007 | FACP | Selby Town Michael Staley 39 Christian Fox 44, 55 Adam Russell 69 |  | 4-0 |  | Pickering Town | Att: 134 HT: 2-0 |
| W | Sat 8/9/2007 | NCELP | Maltby Main Ashley Longstaff 16 Daniel Payne 46, 73 |  | 3-4 |  | Pickering Town Mark Swales 10 Liam Salt 58, 69 James Drinkall 81 | Att: 35 HT: 1-1 |
| D | Wed 12/9/2007 | NCELP | Shirebrook Town Craig Short 43 |  | 1-1 |  | Pickering Town Michael MacNaughton 90 | Att: 40 HT: 1-0 |
| W | Sat 15/9/2007 | NCELP | Pickering Town Mark Swales 1, 19, 21 Gavin Cooper 28og Chris Batchelor 40, 79 |  | 6-3 |  | Brodsworth Welfare Ryan Malee 41, 72 Liam O'Neill 88 | Att: 95 HT: 5-1 |
| L | Tue 18/9/2007 | PC1 | Pickering Town |  | 0-1 |  | Nostell Miners Welfare Danny Highley 46 | Att: 108 HT: 0-0 |
| W | Sat 22/9/2007 | FAV2Q | Brandon United |  | 0-5 |  | Pickering Town Ricky Greening 28, 90 Richard Whitfield 45 Lee Pallender 61 Steve Baxter 75 | Att: 34 HT: 0-2 |
| W | Sat 29/9/2007 | NCELP | Pickering Town Matthew Biggins 77 Richard Whitfield 90 |  | 2-0 |  | Maltby Main | Att: 91 HT: 0-0 |
| October |
| W | Tue 2/10/2007 | NCELP | Long Eaton United |  | 0-2 |  | Pickering Town Matthew Biggins 21, 73 | Att: 42 HT: 0-1 |
| W | Sat 6/10/2007 | FAV1 | Tow Law Town Peter Watling 11 Gavin Mudd 26 |  | 2-3 |  | Pickering Town Michael MacNaughton 27 Ricky Greening 34 Chris Batchelor 48 | Att: 129 HT: 2-2 |
| W | Sat 13/10/2007 | NCELP | Pickering Town Mark Swales 43 Richard Whitfield 45 |  | 2-1 |  | Hallam Robert Cam 73 | Att: 64 HT: 2-0 |
| W | Sat 20/10/2007 | NCELP | Pickering Town Chris Batchelor 7 Ricky Greening 49, 85, 89 Michael MacNaughton 51 |  | 5-0 |  | South Normanton Athletic | Att: 99 HT: 1-0 |
| W | Tue 23/10/2007 | NRSC2P | Pickering Town Mark Swales 17 Rob Eeles 30 |  | 2-1 |  | Marske United Anthony Roberts 48 | Att: 79 HT: 2-0 |
| W | Sat 27/10/2007 | NCELP | Selby Town Brenton Leister 31pen Christian Fox 80 |  | 2-3 |  | Pickering Town Mark Swales 45, 88 Steve Baxter 82 | Att: 86 HT: 1-1 |
| November |
| W | Sat 3/11/2007 | NCELP | Pickering Town Danny Gildea 16 Steve Baxter 43 Ricky Greening 53, 70 Chris Batchelor 73 Liam Salt 90 |  | 6-0 |  | Mickleover Sports | Att: 119 HT: 2-0 |
| D | Sat 10/11/2007 | LC2 | Barton Town Old Boys Craig Burdick 83pen |  | 1-1 (aet) |  | Pickering Town Liam Salt 20 | Att: 92 HT: 0-1 90: 1-1 |
| (Barton Town win 4-2 on pens) |
| W | Tue 13/11/2007 | NCELP | Thackley |  | 0-1 |  | Pickering Town Wayne Aziz 80 | Att: 64 HT: 0-0 |
| D | Sat 17/11/2007 | FAV2 | Eccleshill United Chris Rosindale 61pen |  | 1-1 (aet) |  | Pickering Town Richard Whitfield 23 | Att: 79 HT: 0-1 90: 1-1 |
| W | Tue 20/11/2007 | FAV2R | Pickering Town Ricky Greening 12pen, 67, 90 |  | 3-2 |  | Eccleshill United Chris Rosindale 23pen Paul Baker 44 | Att: 106 HT: 1-2 |
| W | Sat 24/11/2007 | NCELP | Pickering Town Richard Whitfield 2, 31 Chris Batchelor 27 |  | 3-2 |  | Armthorpe Welfare Nathan Iley 6 Henry Sibenge 43 | Att: 120 HT: 3-2 |
| December |
| D | Sat 1/12/2007 | NCELP | Glapwell |  | 0-0 |  | Pickering Town | Att: 97 |
| L | Tue 4/12/2007 | NRSC1 | York City Chris Beardsley 7 Richard Brodie 19, 47 |  | 3-0 |  | Pickering Town | Att: 274 HT: 2-0 |
| L | Sat 8/12/2007 | FAV3 | Winterton Rangers Rob Northen 55 Danny Clarke 89 |  | 2-1 |  | Pickering Town Liam Salt 90 | Att: 142 HT: 0-0 |
| (Winterton Rangers removed from competition - Pickering Town re-instated) |
| W | Sat 22/12/2007 | NCELP | Pickering Town Wayne Aziz 51 Liam Salt 73 |  | 2-0 |  | Glasshoughton Welfare | Att: 101 HT: 0-0 |
| L | Wed 26/12/2007 | NCELP | Pickering Town Liam Salt 75 |  | 1-4 |  | Selby Town Adam Russell 2 Christian Fox 61 Bruno Holden 65 Brenton Leister 85 | Att: 181 HT: 0-1 |
| W | Sat 29/12/2007 | NCELP | Glasshoughton Welfare |  | 0-4 |  | Pickering Town Mark Swales 28 Wayne Aziz 32 Rob Eeles 33 Liam Salt 38 | Att: 62 HT: 0-4 |
| January |
| W | Sat 12/1/2008 | NCELP | Pickering Town Mark Swales 9, 64pen, 69, 90 |  | 4-1 |  | Lincoln Moorlands Railway Craig Bridge 8 | Att: 131 HT: 1-1 |
| L | Sat 26/1/2008 | FAV4 | Merstham Michael Morgan 4 Matt Francis 70 Mark Simmons 97 Kwabema Agyei 107 |  | 4-2 (aet) |  | Pickering Town Steve Baxter 2, 80 | Att: 320 HT: 1-1 90: 2-2 |
| February |
| D | Sat 9/2/2008 | NCELP | Brodsworth Welfare Darren Fell 88 |  | 1-1 |  | Pickering Town Wayne Aziz 58 | Att: 41 HT: 0-0 |
| W | Sat 16/2/2008 | NCELP | Pickering Town Martin Rowbottom 5og Wayne Aziz 24 Ricky Greening 62 |  | 3-1 |  | Shirebrook Town Michael MacNaughton 60og | Att: 124 HT: 2-0 |
| L | Sat 23/2/2008 | NCELP | Arnold Town Craig Mitchell 9, 12 Ashley Harrison 30 |  | 3-0 |  | Pickering Town | Att: 94 HT: 3-0 |
| March |
| W | Sat 1/3/2008 | NCELP | Pickering Town Tom Adams 7 Ricky Greening 59 Liam Salt 75 |  | 3-2 |  | Thackley Joel Ettiene 25 Ian Horrocks 81 | Att: 97 HT: 1-1 |
| W | Tue 4/3/2008 | NCELP | Pickering Town Brian Dutton 27 |  | 1-0 |  | Liversedge | Att: 98 HT: 1-0 |
| L | Sat 8/3/2008 | NCELP | Hallam James Tevendale 11, 36 Will Tomlinson 80 |  | 3-0 |  | Pickering Town | Att: 50 HT: 2-0 |
| W | Sat 15/3/2008 | NCELP | South Normanton Athletic |  | 0-1 |  | Pickering Town Danny Brunton 33 | Att: 59 HT: 0-1 |
| W | Tue 18/3/2008 | NCELP | Pickering Town Richard Whitfield 51 |  | 1-0 |  | Nostell Miners Welfare | Att: 127 HT: 0-0 |
| L | Tue 25/3/2008 | NCELP | Eccleshill United Jarrod Peltier 85 |  | 1-0 |  | Pickering Town | Att: 45 HT: 0-0 |
| D | Sat 29/3/2008 | NCELP | Mickleover Sports |  | 0-0 |  | Pickering Town | Att: 78 |
| April |
| L | Sat 5/4/2008 | NCELP | Pickering Town |  | 0-1 |  | Arnold Town Simon Hore 89 | Att: 100 HT: 0-0 |
| W | Tue 8/4/2008 | NCELP | Pickering Town Richard Whitfield 57 Joe Connor 89pen |  | 2-1 |  | Eccleshill United Marcus Edwards 52 | Att: 66 HT: 0-0 |
| D | Sat 12/4/2008 | NCELP | Armthorpe Welfare |  | 0-0 |  | Pickering Town | Att: 32 |
| W | Tue 15/4/2008 | NCELP | Pickering Town Joe Connor 14 Ricky Greening 82 |  | 2-0 |  | Winterton Rangers | Att: 129 HT: 1-0 |
| W | Sat 19/4/2008 | NCELP | Pickering Town Ricky Greening 45pen Danny Gildea 60 Chris Batchelor 75 |  | 3-0 |  | Long Eaton United | Att: 93 HT: 1-0 |
| L | Tue 22/4/2008 | NCELP | Pickering Town Joe Connor 80pen |  | 1-2 |  | Glapwell Michael Fox 65pen Ian Brown 75 | Att: 119 HT: 0-0 |
| W | Sat 26/4/2008 | NCELP | Parkgate Ryan Johnson 80 Gavin Allott 90 |  | 2-3 |  | Pickering Town Jamie Williamson 10 Steve Baxter 48 Danny Gildea 55 | Att: 38 HT: 0-1 |
| L | Tue 29/4/2008 | NCELP | Pickering Town |  | 0-1 |  | Parkgate Richard Patterson 45 | Att: 135 HT: 0-1 |