Twelve months ago, Tottenham bowed out of the Europa League at the hands of Fiorentina and exited a domestic cup competition within a week.
Unless Spurs can improve on their first-leg showing seven days ago, a double-disappointment is once again on the cards.
The 1-0 home loss to Crystal Palace in the FA Cup was frustrating but has not been deemed a catastrophe with two other competitions to play for.
In both the first leg and the FA Cup defeat, Spurs clearly outplayed their opponent in the first half but faded badly in the second.
What is, for now, merely a coincidence, may yet become a nasty trend.
Atalanta 2-3 Fiorentina
Fiorentina 1-1 Tottenham
Fiorentina 2-1 Inter
Bologna 1-1 Fiorentina
Fiorentina 2-1 Carpi
Spurs 0-1 Palace
Fiorentina 1-1 Spurs
Man City 1-2 Spurs
Spurs 1-0 Watford
Norwich 0-3 Spurs
The team news is mixed for Tottenham ahead of this match. Inspirational goalkeeper and captain Hugo Lloris returns from his shoulder injury, while Erik Lamela is also back after illness. On the other side of the ledger, Harry Kane (broken nose) and Mousa Dembele (groin) will miss out.
Tino Costa, the midfielder who played 66 minutes of the first leg, is out of the return leg, while reserve goalkeeper Sepe has been dropped, and January signing Yohan Benalouane remains sidelined, according to Football Italia.
Paulo Sousa also says Fiorentina's star playmaker Borja Valero "won't be on the pitch."
Defence—Kieran Trippier, Toby Alderweireld, Kevin Wimmer, Ben Davies
Midfield—Ryan Mason, Eric Dier, Josh Onomah, Christian Eriksen, Erik Lamela
Defence—Gonzalo Rodriguez, Manuel Pasqual, Davide Astori, Marcos Alonso
Midfield—Jakub Blaszczykowski, Matias Fernandez, Milan Badelj, Matias Vecino, Filippo Bernardeschi
Player to Watch Per Side
In Valero's absence and needing a goal to secure their progress to the next round, another of Fiorentina's midfielders must step up.
Bernardeschi scored a fortunate goal in the first leg, but that should not obscure the young Italian's rather impressive performance.
His ability to find space between the lines to operate could see him assume the playmaking role for the visitors at White Hart Lane.
Nacer Chadli is the man handed the not insignificant challenge of replacing Harry Kane in Spurs' lineup.
In the first leg, Chadli got his goal but struggled with some of the hold-up play and more creative movements that make Kane such a special player.
Chadli is not really the sort of player who dominates games, but he will need to put his genuine physical power to use in the second leg if Tottenham are to progress.
His pace and goalscoring knack will also make him a threat on the break as La Viola push for their goal.
In the first leg, Sousa got his starting lineup badly wrong, and Spurs had the run of Stadio Artemio Franchi, but he made key changes for the second half and got the upper hand.
Opting to flood the midfield with bodies deprived Mauricio Pochettino's side of the numerical superiority they'd enjoyed in the opening period.
For two teams that usually dominate possession, the midfield is where the game is won and lost.
Spurs are missing one of their key midfielders in Dembele, so Pochettino must carefully select his replacement.
The return of Erik Lamela, the most aggressive and hard-working presser in Spurs' squad, will help them to win this key battle and put them in position to see out the tie.
Live Stream, TV Info
UK: BT Sport, 8:05 p.m.
USA: ESPN 3, 12:05 p.m. (West Coast)
It may not be a popular bet with many of this article's readers, but Fiorentina at 4-1 to win this match is a hugely valuable bet. Spurs deserve favouritism on the basis of their first-leg performance and home advantage, but those are generous odds.
The 10-1 odds offered on a goalless draw also seem to be of good value, given that Tottenham have a rigid defence and would happily take such a result.
Odds courtesy of Oddschecker.