Former Hartlepool United midfielder Tommy Widdrington will make a Victoria Park return with Macclesfield.
Widdrington helped Pool to promotion in 2003 before being released. He was recently appointed captain at Moss Rose under boss Brian Horton.
Pool's home record with Macclesfield is a miserable one - they have yet to record a win in six attempts, losing their last two League encounters and being trounced 4-1 in 2000 and 4-2 in a 1997 FA Cup reverse.
Horton said: "It's a tough game because they had an excellent season.''
Mark Wright's Chester, promoted from the Conference in May, will be the Sunderland's first home game of the campaign - following the trip to Peter Reid's Coventry City on August 7.
The two clubs last met in the League Cup six years ago when goals from Martin Scott, Kevin Phillips, Michael Bridges and Allan Johnston secured a 4-0 aggregate victory.
And there will be a reunion in Darlington, as striker Barry Conlon makes a swift return to the New Stadium with Barnsley on August 24.
After three years in the North-East with Quakers, Conlon moved to Oakwell on a free transfer last month, signing a two-year deal with the Tykes.
And speaking ahead of his Barnsley debut against St Medard in France last night, the 25-year-old revealed his delight at the draw.
"We all heard the draw earlier today and I'm already looking forward to it," said Conlon.
"It will be good to see all the lads again. I've spoken to one or two of them and I know that Hodgy has really been putting them through their paces.
"We know each others strengths and weaknesses so it should be an interesting game."
And after Conlon's 14 goals helped stave off the threat of relegation last season, the Dubliner is predicting brighter times ahead for Quakers.
"I think the fans deserve something to shout about and I think they have the players there to do well," said Conlon. "Hopefully it will be a good year for them."
The sides last met in the same competition ten years ago when they drew 2-2 on aggregate, before the Tykes made it through to the second round on away goals. Next month's encounter will be settled on the night.
DRAW: Lincoln City v Derby County, Sunderland v Chester City, Darlington v Barnsley, Hull City v Wrexham, Nottingham Forest v Scunthorpe, Rochdale v Wolverhampton, Bradford City v Notts County, Bury v Burnley, Tranmere Rovers v Shrewsbury, Crewe Alexandra v Blackpool, Mansfield Town v Preston North End, Sheffield Wednesday v Walsall, Sheffield Utd v Stockport County, Hartlepool Utd v Macclesfield Town, Doncaster Rovers v Port Vale, Oldham Athletic v Stoke City, Grimsby Town v Wigan Athletic, Rotherham Utd v Chesterfield, Leeds Utd v Huddersfield Town, Colchester Utd v Cheltenham Town, Peterborough Utd v Milton Keynes Dons, Gillingham v Northampton Town, Brighton & Hove Albion v Bristol Rovers, Leyton Orient v AFC Bournemouth, Wycombe Wanderers v Bristol City, Boston Utd v Luton Town, Watford v Cambridge Utd, QPR v Swansea City, Kidderminster Harriers v Cardiff City, West Ham Utd v Southend Utd, Ipswich Town v Brentford, Rushden & Diamonds v Swindon Town, Oxford Utd v Reading, Yeovil Town v Plymouth Argyle, Coventry City v Torquay Utd
l ties played week of August 23.
Comments: Our rules
We want our comments to be a lively and valuable part of our community - a place where readers can debate and engage with the most important local issues. The ability to comment on our stories is a privilege, not a right, however, and that privilege may be withdrawn if it is abused or misused.
Please report any comments that break our rules.
Read the rules hereComments are closed on this article