Of the National League Clubs through, North side Guiseley were rewarded for their victory over Cambridge United with a home tie against third-tier Fleetwood Town.
Tim Flowers’ Solihull Moors will host former Premier League side Blackpool, while Wrexham face fellow Welsh club Newport County.
Elsewhere, National League South Woking face a trip to Swindon Town.
All ties will be played on the weekend of November 30 and clubs who progress will receive £54,000.
FA Cup Second Round draw:
Guiseley v Fleetwood Town
Wrexham v Newport County
Tranmere Rovers v Southport
Solihull Moors v Blackpool
Chesterfield v Grimsby Town
Swindon Town v Woking
Maidstone United v Oldham Athletic
FC Halifax Town v AFC Wimbledon
Barnet v Stockport County
Slough Town v Gillingham