Chesterfield have dumped the 2008 winners, Portsmouth, out of the FA Cup in the first round – earning a home tie against Leyton Orient in the second round, while eighth-tier Cray Valley (PM) equalised to set up a replay at home to League One Charlton.

Tom Naylor scored the only goal for Paul Cook’s Chesterfield side, heading Liam Mandeville’s free-kick into the back of the net in the 32nd minute against his former club. Colby Bishop’s header was kept out by Harry Alfred Tyrer while Abu Kamara headed wide from Paddy Lane’s cross as League One leaders Pompey tried to find a leveller.

AFC Wimbledon v Ramsgate; Aldershot Town v Stockport County; Alfreton Town v Walsall; Blackpool v Scarborough or Forest Green; Bolton v Harrogate Town; Cambridge United v Fleetwood Town; Chester or York City v Wigan; Chesterfield v Leyton Orient; Crewe or Derby v Bristol Rovers; Eastleigh v Reading; Gillingham v Charlton or Cray Valley; Maidstone United v Barrow; Newport County v Barnet; Notts County v Shrewsbury; Oxford United v Slough or Grimsby; Peterborough or Salford v Doncaster or Accrington; Stevenage v Port Vale or Burton; Sutton United v Barnsley or Horsham; Wrexham v Yeovil Town; Wycombe v Morecambe.

Ties to be played over weekend of 2-3 December.

Ryan Colclough almost doubled Chesterfield’s lead late on, but the National League leaders and 1997 FA Cup semi-finalists had done enough to advance to the second round, where they will face another League One side in Orient.

Isthmian League South East side Cray Valley earned a replay after a 1-1 draw with Charlton in front of 2,000 of their fans at The Valley. Scott Fraser put the home side in front after just nine minutes, but the visitors drew level when a cross by Kyrell Lisbie – whose father Kevin used to play for The Addicks – was turned into the home net by Lucas Ness early in the second half.

Slough Town were denied a famous win over Grimsby after Danny Rose’s second-half goal cancelled out Scott Davies’ free kick for the National League South side. The winners of the replay will travel to Oxford United in the next round, while Fleetwood will visit Cambridge United after fighting back to beat Kidderminster on Sunday.

Related: FA Cup roundup: Aldershot thrash Swindon 7-4, Stevenage deny Tranmere

Derby County produced a dramatic late fightback to avoid defeat at League Two side Crewe, who led 2-0 with 89 minutes on the clock. Nathaniel Mendez-Laing pulled the first goal back for the visitors before Conor Hourihane struck in the 93rd minute to force a replay, with the winners hosting Bristol Rovers in the next round.

In other standout fixtures from the draw, Aldershot, who beat Swindon 7-4 on Saturday, will host League Two leaders Stockport, while National League South leaders Yeovil Town travel to Wrexham. Eighth-tier Ramsgate’s reward for beating Woking 2-1 in the first round is a trip to AFC Wimbledon.

Horsham, who drew 3-3 with Barnsley on Friday night, will go to League Two strugglers Sutton if they can overcome the Tykes in a replay. Crisis-hit Reading face a tricky trip to Eastleigh, Alfreton Town will entertain Walsall, Maidstone host Barrow and either Chester or York City will host the 2013 Cup winners, Wigan Athletic.