| July |
| D | Sat 16/7/2005 | Frdly | Pocklington Town Anthony Andrews 72 David O'Conner 89 |  | 2-2 |  | Pickering Town Daniel Gray 30 Mark Wood 84 | HT: 0-1 |
| W | Sat 23/7/2005 | Frdly | West Auckland Town David Bayles 44 |  | 1-4 |  | Pickering Town Daniel Gray 32 Steve Young 57, 86 Jon Newton 70 | Att: 56 HT: 1-1 |
| L | Tue 26/7/2005 | Frdly | Pickering Town Daniel Gray 55 |  | 1-2 |  | Newcastle United U19s Marc Walton 31, 33 | HT: 0-2 |
| August |
| L | Sat 6/8/2005 | Frdly | Tadcaster Albion |  | 2-1 |  | Pickering Town Michael McNaughton | |
| L | Tue 9/8/2005 | Frdly | Pickering Town Michael McNaughton |  | 1-2 |  | Leeds United U19s | |
| L | Fri 12/8/2005 | Frdly | Pickering Town Daniel Gray |  | 1-5 |  | Farsley Celtic | |
| W | Sat 20/8/2005 | FACEP | Bacup Borough |  | 0-5 |  | Pickering Town Steve Baxter 67 Steve Roberts 70 Adam Ryan 73, 82 Liam Salt 88 | Att: 40 HT: 0-0 |
| D | Fri 26/8/2005 | FACP | Pickering Town Rob Eeles 43 Liam Salt 87 |  | 2-2 |  | Ashington Wayne Rigg 64, 68 | Att: 137 HT: 1-0 |
| W | Tue 30/8/2005 | FACPR | Ashington Wayne Rigg 62 |  | 1-2 |  | Pickering Town Daniel Gray 1 Dean MacAuley 72pen | Att: 282 HT: 0-1 |
| September |
| D | Sat 3/9/2005 | NCELP | Harrogate Railway Damien Henderson 66 |  | 1-1 |  | Pickering Town Dean MacAuley 25pen | Att: 106 HT: 0-1 |
| D | Wed 7/9/2005 | NCELP | Maltby Main Andrew Wood 44 |  | 1-1 |  | Pickering Town Rob Eeles 53 | Att: 41 HT: 1-0 |
| L | Sat 10/9/2005 | FAC1Q | Pickering Town Liam Salt 84 |  | 1-2 |  | Farsley Celtic Lee Duxbury 51 Curtis Bernard 63 | Att: 147 HT: 0-0 |
| L | Sat 17/9/2005 | NCELP | Pickering Town |  | 0-1 |  | Sutton Town Craig Mitchell 46 | Att: 86 HT: 0-0 |
| W | Sat 24/9/2005 | NCELP | Shirebrook Town Rob Orton 76 |  | 1-2 |  | Pickering Town Mark Swales 2, 50 | Att: 110 HT: 0-1 |
| W | Tue 27/9/2005 | NCELP | Pickering Town Lee Nogan 39, 51 Michael McNaughton 47 Mark Swales 61 Steve Baxter 81 |  | 5-1 |  | Thackley Joel Ettiene 89 | Att: 74 HT: 1-0 |
| October |
| W | Sat 1/10/2005 | NCELP | Long Eaton United |  | 0-1 |  | Pickering Town Steve Swailes 29 | Att: 76 HT: 0-1 |
| L | Sat 8/10/2005 | NCELP | Armthorpe Welfare Gary Jones 19 |  | 1-0 |  | Pickering Town | Att: 60 HT: 1-0 |
| W | Tue 11/10/2005 | NCELP | Eccleshill United |  | 0-1 |  | Pickering Town Matthew Morton 88 | Att: 29 HT: 0-0 |
| W | Sat 15/10/2005 | NCELP | Pickering Town Steve Baxter 26, 66 Ricky Greening 51 Mark Swales 85 |  | 4-1 |  | Hallam Ashley Longstaff 82 | Att: 106 HT: 1-0 |
| W | Sat 22/10/2005 | NCELP | Arnold Town |  | 0-1 |  | Pickering Town Matthew Morton 79 | Att: 111 HT: 0-0 |
| W | Tue 25/10/2005 | NCELP | Pickering Town Ricky Greening 5 Liam Salt 89 |  | 2-1 |  | Glasshoughton Welfare Carl Silburn 65og | Att: 117 HT: 1-0 |
| W | Sat 29/10/2005 | NCELP | Pickering Town Mark Swales 13, 53 |  | 2-1 |  | Garforth Town Nick Jaggar 7 | Att: 129 HT: 1-1 |
| November |
| W | Tue 1/11/2005 | NRSC1 | Pickering Town Phil Brumwell 17og Lee Pallender 33 |  | 2-0 |  | Whitby Town | Att: 321 HT: 2-0 |
| W | Sat 5/11/2005 | NCELP | Buxton Andrew Brownrigg 4 Stewart Copnell 23 |  | 2-3 |  | Pickering Town Steve Roberts 46 Mark Swales 60 Steve Baxter 64 | Att: 582 HT: 2-0 |
| W | Sat 12/11/2005 | LC2 | Yorkshire Amateur Adam Ryder 50 |  | 1-2 |  | Pickering Town Rob Eeles 19 Liam Salt 75 | Att: 42 HT: 0-1 |
| W | Sat 19/11/2005 | FAV2 | Pickering Town Liam Salt 103 |  | 1-0 (aet) |  | Oldham Town | Att: 115 HT: 0-0 90: 0-0 |
| D | Sat 26/11/2005 | NCELP | Pickering Town |  | 0-0 |  | Glapwell | Att: 82 |
| L | Tue 29/11/2005 | PC1 | Pickering Town Steve Roberts 15 |  | 1-3 |  | Selby Town Ian Twitchen 2, 17, 71 | Att: 135 HT: 1-2 |
| December |
| W | Sat 3/12/2005 | NCELP | Pickering Town James Drinkall 7 Steve Baxter 32 Michael McNaughton 73pen |  | 3-2 |  | Eccleshill United Andrew Patterson 26 Jamie Buchan 85pen | Att: 111 HT: 2-1 |
| W | Sat 10/12/2005 | FAV3 | Pickering Town Lee Nogan 3 |  | 1-0 |  | Dunston Federation Brewery | Att: 131 HT: 1-0 |
| L | Sat 17/12/2005 | NCELP | Sheffield Robert Ward 65pen |  | 1-0 |  | Pickering Town | Att: 145 HT: 0-0 |
| L | Mon 26/12/2005 | NCELP | Pickering Town |  | 0-1 |  | Liversedge Gareth Hamlet 26 | Att: 175 HT: 0-1 |
| January |
| D | Mon 2/1/2006 | NCELP | Glasshoughton Welfare Adam Sadler 83 |  | 1-1 |  | Pickering Town James Drinkall 45 | Att: 105 HT: 0-1 |
| W | Sat 7/1/2006 | NCELP | Pickering Town Steve Swailes 2 Ricky Greening 12 James Drinkall 25 Josh Watts 90og |  | 4-2 |  | Long Eaton United Steven Young 28 Carl Adams 83 | Att: 81 HT: 3-1 |
| L | Sat 14/1/2006 | NCELP | Sutton Town Michael Fox 1 Mark Hurst 42 Barry Stokes 45 Craig Mitchell 90 |  | 4-2 |  | Pickering Town James Drinkall 40 Lee Nogan 50 | Att: 93 HT: 3-1 |
| W | Sat 21/1/2006 | FAV4 | Pickering Town Lee Nogan 46 James Drinkall 56 Steve Swailes 69 |  | 3-0 |  | Tavistock | Att: 290 HT: 0-0 |
| W | Tue 24/1/2006 | LC3 | Pickering Town Craig Beastall 85og |  | 1-0 |  | Glapwell | Att: 100 HT: 0-0 |
| W | Sat 28/1/2006 | NCELP | Brodsworth Welfare Gareth North 40 |  | 1-2 |  | Pickering Town Lee Nogan 64, 74 | Att: 32 HT: 1-0 |
| February |
| L | Wed 1/2/2006 | NRSC2 | Northallerton Town Ross Diamond 29 Karl Charlton 30 |  | 2-1 |  | Pickering Town Lee Nogan 34 | Att: 96 HT: 2-1 |
| D | Sat 4/2/2006 | NCELP | Mickleover Sports |  | 0-0 |  | Pickering Town | Att: 97 |
| D | Tue 7/2/2006 | NCELP | Pickering Town |  | 0-0 |  | Harrogate Railway | Att: 127 |
| W | Sat 11/2/2006 | FAV5 | Wimborne Town Sam Percival 30 |  | 1-2 |  | Pickering Town James Drinkall 47 Liam Salt 71 | Att: 983 HT: 1-0 |
| D | Tue 14/2/2006 | LCQF | Selby Town Tom Reid 104 |  | 1-1 (aet) |  | Pickering Town Julian Wilkes 116 | Att: 52 HT: 0-0 90: 0-0 |
| (Replay: Tue 21st Feb) |
| L | Sat 18/2/2006 | NCELP | Thackley Mark Senior 87 |  | 1-0 |  | Pickering Town | Att: 79 HT: 0-0 |
| L | Tue 21/2/2006 | LCQFR | Pickering Town James Drinkall 65 Danny Brunton 78 |  | 2-4 |  | Selby Town Ian Twitchen 3, 71 Andrew Dawson 14 Tom Matthews 49 | Att: 124 HT: 0-2 |
| W | Sat 25/2/2006 | NCELP | Pickering Town Dean MacAuley 1 Danny Brunton 24 |  | 2-0 |  | Brodsworth Welfare | Att: 64 HT: 2-0 |
| March |
| L | Sun 12/3/2006 | FAV6 | Nantwich Town Matt Blake 15 Danny Griggs 85 |  | 2-0 |  | Pickering Town | Att: 698 HT: 1-0 |
| D | Sat 18/3/2006 | NCELP | Liversedge Paul Walker 47, 63 |  | 2-2 |  | Pickering Town Steve Baxter 26 Dean MacAuley 80pen | Att: 146 HT: 0-1 |
| W | Tue 21/3/2006 | NCELP | Garforth Town |  | 0-2 |  | Pickering Town Dean MacAuley 13 Mark Swales 80 | Att: 92 HT: 0-1 |
| L | Sat 25/3/2006 | NCELP | Pickering Town |  | 0-1 |  | Buxton Shaun Doxey 81 | Att: 157 HT: 0-0 |
| April |
| L | Wed 5/4/2006 | NCELP | Hallam Richard Lopes 9 Ashley Longstaff 12 Tom Franklin 27 |  | 3-1 |  | Pickering Town Liam Salt 53 | Att: 65 HT: 3-0 |
| W | Sat 8/4/2006 | NCELP | Pickering Town James Drinkall 16 Liam Salt 25 |  | 2-0 |  | Maltby Main | Att: 74 HT: 2-0 |
| D | Tue 11/4/2006 | NCELP | Pickering Town Ricky Greening 49 Mark Swales 68, 71 |  | 3-3 |  | Armthorpe Welfare | Att: 76 |
| W | Sat 15/4/2006 | NCELP | Glapwell Mark Robinson 82 |  | 1-4 |  | Pickering Town Lee Nogan 6 Michael McNaughton 49 Steve Roberts 55 Mark Swales 59 | Att: 60 HT: 0-1 |
| W | Mon 17/4/2006 | NCELP | Pickering Town Mark Swales 43, 45, 78 Rob Eeles 66 Steve Roberts 80 Ricky Greening 83 |  | 6-1 |  | Shirebrook Town Glen Holland 20 | Att: 113 HT: 2-1 |
| D | Wed 19/4/2006 | NCELP | Pickering Town Lee Nogan 85 |  | 1-1 |  | Sheffield Robert Ward 76 | Att: 101 HT: 0-0 |
| W | Sat 22/4/2006 | NCELP | Pickering Town Dean MacAuley 84pen, 85pen |  | 2-0 |  | Mickleover Sports | Att: 95 HT: 0-0 |
| L | Tue 25/4/2006 | NCELP | Pickering Town Danny Brunton 83 |  | 1-2 |  | Arnold Town Tony Brown 50 Ben Middleton 51 | Att: 101 HT: 0-0 |
| W | Sat 29/4/2006 | NCELP | Pickering Town Ricky Greening 13 |  | 1-0 |  | Selby Town | Att: 117 HT: 1-0 |
| May |
| L | Mon 1/5/2006 | NCELP | Selby Town Tom Hogg 6 Tom Matthews 69 Ian Twitchen 79pen Joe Connor 86pen |  | 4-1 |  | Pickering Town Dominic Graham 53 | Att: 50 HT: 1-0 |