Graeme Lee will perform a selection juggling act when Boro Under-23s travel to Crystal Palace on Monday (1pm).
Boro head for Selhurst Park knowing that victory could be enough to guarantee a place in the end of season PL2 play-offs with one game still to play.
Just five points separate six clubs - from third-placed Wolves down to Palace in eighth - and Monday is a pivotal day in the calendar with play-off chasing Boro (4th) at Palace, and Burnley (5th) and Sunderland (6th) in action.
Leeds, who play Burnley on Monday, are already crowned champions, and Stoke will take the play-off place awarded to the club who finishes second.
With a number of his young charges on the bench for the first team at Luton on Saturday and with the U17 PL Cup final against Brighton on Wednesday, Lee will have plenty to think about in terms of balancing his selection for the game.
Our 23s are also in action again on Friday when they meet Palace for the second time in the space of five days in the final game of the regular season and the first team take on Wycombe Wanderers the following day at the Riverside in the last senior outing of the campaign.
Crystal Palace are streaming Monday's game live and have told us: "All supporters can purchase a one-off, pay-per-view pass to watch the match. For just £3, this pass can be purchased from 10:00am BST on Monday (2nd), and will enable you to watch the broadcast via your phone, tablet or desktop.
"To purchase a pay-per-view pass, head over to Palace TV, log-in or sign-up for a Palace Account and purchase your pass for £3."