Uefa Cup round-up:English dominance in Europe appears to be restricted to the Champions League after Spurs and Everton suffered defeat, and Bolton were held at home, in their Uefa Cup fourth round first leg ties.
Rangers were the only British side to emerge victorious with a 2-0 win over Werder Bremen at Ibrox.
Everton had no answer to two pedigree second-half goals as they went down 2-0 away to Fiorentina in Florence.
After a first half in which Everton were off the pace — and doubtless relieved to still be level — Zdravko Kuzmanovic and then Riccardo Montolivo each produced a memorable finish to confirm the Italians' superiority.
It was harsh on Everton goalkeeper Tim Howard, who had come to his team's rescue with a succession of outstanding saves — but otherwise the Toffees got their just deserts.
Gilberto suffered a nightmare Tottenham debut at White Hart Lane as PSV Eindhoven earned a slender advantage to take to Holland next week.
Spurs coach Juande Ramos billed this last-16 clash as the barometer of whether his side could win the Uefa Cup — but it was the Dutch champions that looked more likely to be at Eastlands in May.
Although it was a deflating evening for Ramos' players, none were as disappointing as Gilberto; the Brazil full-back was booked, was at fault for Jefferson Farfan's winner and was taken off at half-time.
Bolton will have to conjure another of their Uefa Cup away-day specials if this season's adventure is to continue.
The odds of reaching the quarter-finals are now stacked heavily in favour of Sporting Lisbon after Simon Vukcevic cracked a stunning equaliser to cancel out Gavin McCann's first-half opener.
But Gary Megson's side cannot be discounted as they have produced some remarkable results on their travels, notably in beating Red Star Belgrade and drawing with Bayern Munich and Atletico Madrid.
Steve Davis opened his goalscoring account as Rangers took a major step towards the last eight
Davis sealed the win early in the second half after Daniel Cousin put his failed move to Fulham firmly behind him with a goal on the stroke of half-time.
Uefa Cup fourth round results
Anderlecht 0-5 Bayern Munich
Bayer Leverkusen 1-0 Hamburg
Benfica 0-2 Getafe
Bolton 1-1 Sporting
Fiorentina 2-0 Everton
Marseille 3-1 Zenit St Petersburg
Rangers 2-0 Werder
Tottenham 0-1 PSV
