Newcastle must play at Stevenage while Boro will go to Burton Albion.
The last time the Magpies travelled to Stevenage's Broadhall Way was in 1998 and Alan Shearer and Co were forced to a replay at St James' Park by the non-league club en route to a Wembley final.
Thirteen years later and Chris Hughton's class of 2010- 11 are going to have to negotiate them again after yesterday being paired with them for a second time.
The weekend of January 8, 2011, will also see Middlesbrough, struggling at the wrong end of the Championship, face a tricky trip to Burton Albion.
It will be the first time the two clubs have met and could also present an opportunity for Burton's former Middlesbrough and Hartlepool goalkeeper Kevin Poole to face his old team at the ripe old age of 47.
Sunderland have also been handed lower league opposition, although their tie should be easier. The Black Cats will face either Paul Ince's Notts County or Bournemouth, once they have played their second round replay, at the Stadium of Light.
There is a tough challenge ahead for Hartlepool United if they can overcome Yeovil Town in their rearranged second tie on Tuesday, December 7.
Pools have been handed a trip to Championship club Watford, where Hartlepoolborn Andrew Taylor is currently on loan from Middlesbrough until early January initially, if they can progress.
If Hartlepool can set up a date at Vicarage Road and pull off a shock it would be worth £67,500 in prize money alone, not to mention a lucrative fourth round tie.
That is the reward on offer for any of the clubs in the third round, including Darlington's conquerors York City, who have been handed a trip to Premier League opposition Bolton Wanderers.
Elsewhere the pick of the draw is undoubtedly at Old Trafford, where Liverpool have been handed the unwanted but mouthwatering clash with rivals Manchester United.
FC United of the Evostick League, provided they can win their replay with League One leaders Brighton at Gigg Lane, have been drawn at home to Portsmouth. While Dover athletic, of the Blue Square South, will travel to Huddersfield Town.
Droylsden, of the Blue Square Bet North Division, face League One Leyton Orient this evening with a trip to Norwich the prize for the winners.