It was the Dnipro head coach who masterminded Tottenham's last trophy triumph as he won the League Cup in February 2008.
Eight months later, however, the Spaniard was sacked with the London club bottom of the Premier League and Ramos now heads back to White Hart Lane attempting to protect a 1-0 lead following the first leg of the last-16 tie between the two sides last Thursday.
The odds appear to be stacked against Dnipro – fourth in the Ukrainian Premier League – reaching the quarter-finals given Tottenham's formidable home record in the competition.
Tottenham have suffered just one defeat in their last 18 Europa League ties at White Hart Lane, winning 12 of those matches, including the last four in a row this season.
|11/1||Tottenham are 11/1 with Paddy Power to win the Europa League|
Goalkeeper Hugo Lloris and winger Aaron Lennon also missed the defeat in Ukraine but could return.
In addition, Sherwood will expect his side to be more ruthless in attack as Roberto Soldado was guilty of a poor miss in the first leg before Yevhen Konoplyanka netted from the penalty spot.
"We will score at the Lane, guaranteed," said Sherwood.
Perhaps some of Sherwood's optimism stems from the fact that the playing conditions will suit Tottenham this time around.
A major talking point from the first leg was the state of the Dnipro Arena's pitch, which Sherwood labelled a "disgrace" after seeing the ball bobble badly on an uneven surface.
The two sets of players will experience no such problems on Thursday, although Tottenham could be short on confidence following Sunday's 1-0 defeat at Norwich City.
Midfielder Etienne Capoue sustained a leg injury during the loss at Carrow Road which makes him a doubt.
Dnipro, meanwhile, should feel fresh as Ramos' men had a free weekend due to the fact that the Ukrainian Premier League is still on its mid-season break.
Either PAOK or Benfica await the winners in the next round.