Tottenham Hotspur will look to progress to the fourth round of the FA Cup at the second time of asking when they welcome Championship side Middlesbrough to North London for a third-round replay on Tuesday night.
Middlesbrough's management team of Jonathan Woodgate and Robbie Keane were both in the Tottenham side the last time Spurs won a trophy, with Woodgate scoring the winner in the League Cup final 12 years ago.
Now, they will be attempting to devise a plan to knock their former club out of the FA Cup on their own turf, although in Mourinho they come up against a manager picked specifically to end that Tottenham wait for silverware.
Somewhat surprisingly, Mourinho has only won the FA Cup once before, and his side were almost dumped out at the first hurdle last weekend when they needed Lucas's 61st-minute strike to cancel out Ashley Fletcher's opener, despite naming a team close to the strongest possible.
Spurs have only failed to make it past the third round once since 2005-06 but go into the match on a four-game winless streak, most recently losing 1-0 at home to Premier League leaders Liverpool on Saturday.
Mourinho was happy with his side's performance in that match despite seeing them miss two golden late chances to steal a point, but injuries to key players such as Harry Kane, Hugo Lloris and Moussa Sissoko do still mean that this is a good time to face Tottenham.
The honeymoon period seems to be over for Mourinho, who has won just three of his last 10 games across all competitions having begun his reign with three successive victories, and the supporters' frustrations were evident for much of Saturday's loss to Liverpool.
A lot of that anger was directed at contract rebel Christian Eriksen, who was jeered off the pitch, and anything other than victory over a team that has been struggling against relegation from the Championship this season is sure to only further upset the home fans.
Things have improved for Boro of late, though, to the point where Woodgate was named the Championship manager of the month for December, having only recently seen his future come under intense scrutiny.
A six-match unbeaten streak across all competitions has lifted Middlesbrough up to 16th, now closer to the playoff places than they are to the relegation zone.
That run includes back-to-back away wins over promotion-chasing duo West Bromwich Albion and Preston North End, having failed to win any of their first 11 matches on the road this season.
Boro have lost their last two FA Cup away games, though, most recently being dumped out by Newport County in the fourth round last term.
Tottenham FA Cup form: D
Tottenham form (all competitions): LWDLDL
Middlesbrough FA Cup form: D
Middlesbrough form (all competitions): WWWWDD
Mourinho sprung a major surprise by selecting Japhet Tanganga for his Premier League debut against Liverpool on Saturday, but the 20-year-old's performance in that match may have been enough to earn him another starting role here.
The likes of Jan Vertonghen, Eric Dier, Ryan Sessegnon and Giovani Lo Celso will be hopeful of a start if Mourinho decides to rotate his squad, although he named a strong team in the initial tie and is unlikely to make wholesale changes.
Middlesbrough are also unable to welcome any of their injury absentees back in time for this match, but Adam Clayton is expected to start in midfield.
Djed Spence, who was linked with a move to Spurs following his performance in the first match, is expected to start at right wing-back once again.
Tottenham possible starting lineup:
Gazzaniga; Tanganga, Dier, Vertonghen; Aurier, Skipp, Winks, Alli, Sessegnon; Lucas, Son
Middlesbrough possible starting lineup:
Tomas; Howson, McNair, Fry; Spence, Clayton, Saville, Coulson; Roberts, Fletcher, Tavernier
We say: Tottenham 2-0 Middlesbrough
Middlesbrough did admirably to force a replay in the first match, but Spurs enjoyed 71% possession at the Riverside and are likely to be even more dominant on the ball in front of their own fans. Winning on their first ever visit to the Tottenham Hotspur Stadium, where not even Liverpool found things straightforward, may be too big an ask for the Championship side.
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