While the visitors will move back into the automatic promotion spots with a win, a dissatisfactory result for Boro will kill off their already-slim playoff hopes.
Match preview
It may be too little too late for Middlesbrough to upset the top-six apple cart, but Michael Carrick's men are at least ending the campaign with a flourish and have the chance to extend their unbeaten run into the double figures when the Whites visit their Riverside home.
A total of 19 points have been accrued from the hosts' last nine Championship affairs - five wins in addition to four stalemates - including back-to-back draws with fellow playoff outsiders Hull City and title-chasing Ipswich Town in their last two fixtures.
The stopover at Portman Road on April 13 saw the in-form Emmanuel Latte Lath continue his hot streak of form, heading in his fourth goal from as many games - and 12th of the season - on the 20-minute mark, but Carrick's men were only in the ascendancy for 10 minutes before Massimo Luongo restored the Tractor Boys' pride.
Entering the gameweek ninth in the rankings with just nine points left to fight for, the hosts have that exact disadvantage to make up to West Bromwich Albion and Norwich City in the final two playoff spots, leaving their playoff hopes hanging by the thinnest of threads.
Gearing up for their penultimate home contest of the 2023-24 season, Middlesbrough ought to be incredibly encouraged by a streak of three consecutive clean sheets at the Riverside - shutting out Blackburn Rovers, Sheffield Wednesday and Swansea City in that time - although only two of their last 10 versus Yorkshire teams on familiar turf have seen Boro come up trumps.
Northern woes may not hold much significance if the form book is anything to go by, though, as while Leicester City's dramatic downturn in fortunes may have made most of the headlines, Leeds have also hit a sticky patch at the most inopportune time.
From January 1 to April 1, Daniel Farke's men were slaying almost every opponent in their wake - taking an astounding 41 points from 45 on offer during a 15-match unbeaten sequence - but Monday's visitors have since gained just a solitary point from the last nine available.
Either side of an uninspiring goalless draw with Sunderland, Farke's troops have been put to the sword by Coventry City and - more alarmingly - bottom-half battlers Blackburn Rovers, who left Elland Road with a 1-0 triumph to their name on April 13 thanks to Sammie Szmodics's 24th of the campaign.
However, thanks to Coventry City reaching the FA Cup semi-finals - leading to the postponement of their clash with Ipswich - third-placed Leeds will temporarily usurp the Tractor Boys, who are two points better off, if they can return to victorious ways at the Riverside on Monday evening.
The Whites therefore possess all the motivation they require to pull themselves out of their rut, and the head-to-head records are on their side too; Leeds have prevailed in each of their last three contests with Middlesbrough, who have not overcome their Yorkshire foes since Patrick Bamford struck a hat-trick in a 3-0 2018 success before his switch to Elland Road.
Middlesbrough Championship form:
D
D
W
W
D
D
Leeds United Championship form:
W
D
W
L
D
L
Team News
Carrick must cope with the loss of one of his attacking and defensive options this week, as Middlesbrough's Leeds loanees Sam Greenwood and Luke Ayling are unable to face their parent club, although the former was only a second-half substitute in the draw with Ipswich anyway.
Ayling's absence should see Anfernee Dijksteel drafted in at right-back, and there is optimism that Paddy McNair will be back in contention following a hamstring injury, but he is the only man in with a shot of exiting the infirmary for Monday's game.
Indeed, all of Hayden Hackney (leg), Riley McGree (foot), Marcus Forss (hamstring), Dael Fry (groin), Josh Coburn (groin), Tom Smith and Darragh Lenihan (both Achilles) remain sidelined, while Tom Glover has undergone finger surgery and will not play again this term.
Likewise, Leeds boss Farke must also make an enforced change on the right-hand side of defence, as Connor Roberts is revealed to have suffered a recurrence of the muscular injury he sustained while playing for Wales last month and will miss two games at the very least.
Archie Gray - recently crowned the Championship's Young Player of the Season - could take up right-back duties in place of the stricken Roberts, in turn allowing Glen Kamara to return to the XI as Ilia Gruev's midfield partner.
Darko Gyabi and Pascal Struijk both underwent season-ending groin operations last month, and off the pitch, Farke's assistant Christopher John was sent off and subsequently charged with improper conduct in the Blackburn defeat, although it is still unknown whether he will be suspended for this one.
Middlesbrough possible starting lineup:
Dieng; Dijksteel, Van den Berg, Clarke, Engel; O'Brien, Howson; Jones, Azaz, Silvera; Latte Lath
Leeds United possible starting lineup:
Meslier; Gray, Ampadu, Rodon, Firpo; Gruev, Kamara; Gnonto, Rutter, Summerville; Piroe
We say: Middlesbrough 1-1 Leeds United
Middlesbrough's brilliant defensive exploits at home spells danger for a Leeds side who have just lost their way a tad in recent weeks, and Carrick's men have performed admirably in the face of injury-related adversity.