Newcastle United 1 Tottenham Hotspur 2
Without a manager and with owner Mike Ashley attempting to sell the club, the Magpies are rudderless and teetering towards the abyss.
Spurs had been little better, without a win in the Premier League to date, but after an appalling first half, they showed what little quality was on offer on the night in the second period to seal their place in the last 16.
The first half was terrible with the only half-chance falling to Charles N'Zogbia whose shot was easily saved by Spurs keeper Heurelho Gomes.
At the other end, Roman Pavlyuchenko headed just wide from a corner but at least both sides moved up through the gears after the break.
Obafemi Martins set up Damien Duff at the start of the second period, but the Republic of Ireland winger's goalbound effort was turned away by the alert Jonathan Woodgate.
Spurs substitute Giovani dos Santos then crossed for Russia international Pavlyuchenko who almost bundled the ball home.
Michael Owen had a shot saved before Spurs took the lead in the 62nd minute when Aaron Lennon crossed for the unmarked Pavlyuchenko to head home his first goal for the club.
Four minutes later Fabricio Coloccini and Steven Taylor combined disastrously to allow Jamie O'Hara to slot Spurs' second past Shay Given and, although Owen pulled a last-gasp goal back for United, it was the visitors who held on to the deserved victory.