The Hoops face a 434 mile round trip to National League North Side Scarborough Athletic in the Fourth Qualifying Round of the Emirates FA Cup.
City come into this game off the back of a strong performance against AFC Fylde in the National League, beating the Coasters 3-0 thanks to a first-half spot-kick from Josh Parker and a second-half brace from Olly Sanderson.
Boro, unlike City, have had to battle through the qualifying rounds to get to this stage.
Fellow league opposition Farsley Celtic were Scarborough's first victims - as Scarborough secured their passage from the Second Qualifying Round after a 3-0 win from a replay.
A narrow victory followed for the Seadogs as they again knocked out National League North opposition. This time, Darlington were beaten with Jonathan Greening's side running out 2-1 winners.
Life in the National League North hasn’t been too pretty so far in this campaign for Scarborough, who sit in 18th with one win to their name in the previous six matches.
This is their second straight season at step 2. City will be hoping to add to last weekend’s victory and will look to have their name in the hat for the First Round Proper, but can the magic of the FA Cup hold them back?
Ross Jenkins has admitted that City are down to the bare bones ahead of the tie.
Josh Ashby remains out for Saturday's match and Nya Kirby is a doubt as the midfielder continues to recover from injury.
Lewis Miccio is nearing a return but a return to action may come too soon for the defender.
Mitchell Roberts made his debut for City in the weekend's victory over AFC Fylde and is eligible to play on Saturday.
Despite two heavy defeats to Oldham and Gateshead, the Hoops bounced back in emphatic style at the weekend, beating AFC Fylde 3-0 at the RAW Charging Stadium.
City are still on the hunt for their first victory away from home this season and with Scarborough’s home form, it won’t be a walk in the park for The Hoops.
Ross Jenkins’ side will be looking to build on the previous result when they take the hefty trip on Saturday afternoon.
With September’s Player of the Month award already to his name, midfielder Lewis Maloney is our ‘One To Watch’.
The experienced 28-year-old has started all 10 games so far this season and has netted three times already, one of his goals helping seal a victory against Brackley Town with a superb effort outside the area, which looped into the top corner.
Maloney has proved to be a crucial player in the Scarborough squad this season, and will undoubtably continue to do so on Saturday afternoon.
Maloney came through Middlesbrough's academy, graduating through the Championship side’s U18’s, through to U21.
He made the free transfer to Marske United from Gateshead, before signing for Scarborough on a free in 2021.
“On paper we’re the higher ranked team, but if you look at the size of the clubs and the attendances, there’s not much between the two clubs.
“It’s going to be difficult for sure. It’s going to be a battle but it’s not like going to an Oldham or a Chesterfield kind of scenario.
“We’re new to the National League and we’ve done well to get here but there’s not a million miles between us.
“They’ll know that and we need to know that. We can’t go there thinking we’re better than anyone because we’ll get rolled over.
“We’ve got to respect them and we’ve got to respect that the National League North is a difficult league."
This will be the first clash between the two clubs. The tie will also be the first time Scarborough will have played opponents from the fifth tier of the football pyramid.
This is also Boro's second ever FA Cup Fourth Qualifying Round tie.
Greening began life in the footballing scene in 1996, and went onto making 473 Club Appearances as a midfielder.
He played for a series of teams (York, Manchester United, Middlesbrough, West Bromwich Albion, Fulham, Nottingham Forest, Barnsley, Tadcaster Albion) before taking up the Coaching role with one of his former clubs, York City.
‘Jono’ signed for Manchester United in 1998, following a four-day trial. Despite facing hefty competition as an attacking midfielder, Grenning made the bench in the ‘99 UEFA Champions League Final, but failed to feature on the pitch.
Greening went on loan to Fulham, before signing for the Middlesex side in 2011. He went onto help Fulham make the UEFA Europa League Final in 2009, before signing for Nottingham Forest on a three-year deal.
His first managerial appointment was at his current club, Scarborough Athletic, in May 2021.
Greening led The Seadogs to promotion from Step 3 to the National League North during his first campaign at the club.
Scarborough had an emphatic start to their first season, sitting in 3rd place by the end of 2022 and just one point from the top spot - a feat that meant that ‘Jono’ took the December Manager of the Month Award.
Boro ended up finishing in a respectable 8th position last season in the National League North.
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Click HERE to head to the BBC's non-league commentary page where you'll be able to tune in at around 14:50. Or simply tune into BBC Radio Oxford on BBC Sounds.