On Saturday two goals from Alvaro Negredo and one from Marten de Roon eased Boro' to victory over Swansea.
However while the Swans' first team is struggling, their U23s are flying and if Boro are to complete a double having won earlier in the season, on Monday night they will have to beat the team sitting seven points clear at the top of the table.
Goals from Arnel Jakupovic and Callum Cooke edged Boro to victory at Hartlepool in September, a result that put them second in the table. But while they have done well in the cups, they haven't won in the league since then.
"I think we have played a lot better in recent games," says Lead Coach Paul Jenkins. "We went through a patch where nothing would work, things just working for us. But we have settled and a change in shape has, I think, helped.
"We saw last Monday against Norwich we have character in the side. We were in front, then had to come from behind to get a point and I thought we did enough to win it.
"We know this game will be tough, Swansea have had a really good, settled season and we respect them a lot. But we're not just there to make up the numbers and we'll give it a right good go."
Kick-off at Swansea's Landore Training Ground is 7pm.