Chesterfield have drawn Portsmouth in the headline tie of the First Round draw in 2023-24 FA Cup.
This clash will see the Spireites meet the Pompey in a blockbuster tie between the current National League and League One leaders at the SMH Group Stadium.
Eighth-tier Cray Valley Paper Mills will visit Charlton Atheltic at The Valley in a South London derby encounter, having previously defeated Enfield Town in a London derby in the Fourth Qualifying Round.
Ramsgate will host the winner of Hemel Hempstead’s replay against Woking in an all Non League encounter.
Should eighth-tier Sheppey United overcome Billericay Town in a replay, they will play host to League Two’s Walsall.
Last season’s Quarter-Finalists, Grimsby Town will visit either Ebbsfleet United or Slough Town who need a replay.
National League’s Bromley will take on 1952-53 winners, Blackpool at Hayes Lane in an intriguing encounter.
First Round ties will be played across 3-6 November with selected fixtures broadcast live across BBC and ITV, whilst all winning clubs awarded £40,000 in prize money and a Second Round spot.
| Team 1 | v | Team 2 |
| Curzon Ashton | v | Barnet |
| Alfreton Town | v | Worthing |
| Chesterfield | v | Portsmouth |
| Bolton Wanderers | v | Solihull Moors |
| Exeter City | v | Wigan Athletic |
| Leyton Orient | v | Carlisle United |
| Kidderminster Harriers | v | Fleetwood Town |
| Hereford | v | Gillingham |
| Slough Town | v | Grimsby Town |
| Charlton Athletic | v | Cray Valley PM |
| Oxford United | v | Maidenhead United |
| Newport County | v | Oldham Athletic |
| Swindon Town | v | Aldershot Town |
| Crewe Alexandra | v | Derby County |
| Mansfield Town | v | Wrexham |
| Marine | v | Harrogate Town |
| Barnsley | v | Horsham |
| Port Vale | v | Burton Albion |
| Peterborough United | v | Salford City |
| Eastleigh | v | Boreham Wood |
| Bradford City | v | Wycombe Wanderers |
| Sheppey United | v | Walsall |
| Shrewsbury Town | v | Colchester United |
| Bristol Rovers | v | Whitby |
| Lincoln City | v | Morecambe |
| Sutton United | v | AFC Fylde |
| Reading | v | MK Dons |
| Doncaster Rovers | v | Accrington Stanley |
| Chester | v | York City |
| Scarborough Athletic | v | Forest Green Rovers |
| Notts County | v | Crawley Town |
| Stockport County | v | Worksop Town |
| Yeovil Town | v | Gateshead |
| Stevenage | v | Tranmere Rovers |
| Chesham | v | Maidstone United |
| Bromley | v | Blackpool |
| AFC Wimbledon | v | Cheltenham Town |
| Cambridge United | v | Bracknell Town |
| Northampton Town | v | Barrow |
| Ramsgate | v | Woking |
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