Title hopefuls Liverpool suffered defeat in their first game of the new Barclays Premier League campaign as Sebastien Bassong scored on his debut in a 2-1 victory for Tottenham at White Hart Lane.
Reds boss Rafael Benitez had spent the summer plotting how to overhaul champions Manchester United, having fallen just short last season in the quest for a first title since 1990.
New arrival Glen Johnson, who cost £17million from Portsmouth, started at right-back, Dutchman Ryan Babel was chosen ahead of Yossi Benayoun with Spain forward Fernando Torres expected to again provide the goals along with captain Steven Gerrard, fit following a groin problem.
Given title rivals United had won earlier on Sunday afternoon, coupled with victories on Saturday for both Chelsea and, most impressively, Arsenal, there was little margin for error if Liverpool were to avoid playing catch up after just one match.
However, the Reds never really got going, with Torres particularly disappointing.
Indeed, Liverpool should have been more than 1-0 down at half-time had Anfield old boy Robbie Keane not missed a couple of clear chances before full-back Benoit Assou-Ekotto smashed in a 25-yard effort past Pepe Reina.
Although the visitors were handed a lifeline back into the match when Johnson was upended by keeper Heurelho Gomes to give away a penalty, which Gerrard converted on 54 minutes, Spurs soon regained the lead as Bassong, an £8million signing from Newcastle, headed in a free-kick from Luka Modric.
While there is, of course, plenty of football left to be played between now and May, Benitez knows his men will have to do much, much better if they are to finish ahead of the rest.
After a slow start, there was a stoppage on 14 minutes when Martin Skrtel and Jamie Carragher collided heads after both jumping for a high ball.
The English defender had to go off for treatment on a bloody gash, before returning with some heavy bandages.
Gerrard let fly with a 25-yard effort, which was just wide of Gomes' right-hand post.
Spurs then really should have gone ahead on 30 minutes.
Wilson Palacios got away down the right, and looped the ball across to the far post.
Modric lofted it back into the six-yard box, where Keane arrived with a diving header - but one which was straight at Reina, who reacted brilliantly.
The Liverpool keeper then denied his former team-mate once again, this time standing up well as Keane tried a chip.
On 44 minutes, Skrtel gave away a free-kick in a dangerous position, some 25 yards out, when he fouled Palacios.
Tom Huddlestone drove his effort into the defenders - but the ball fell kindly for Assou-Ekotto, who promptly smashed it back into the top corner.
Liverpool regrouped at half-time and produced a flowing move when Dirk Kuyt touched the ball back to Torres, who laid it on for Gerrard, but the England midfielder struck his low shot just wide from 20 yards.
A fine fingertip save from Reina then denied Palacios a second goal for Spurs following a rasping 25-yard drive towards the top right corner.
Liverpool found a way back into the match when they were awarded a penalty on 54 minutes.
Johnson was upended by Spurs keeper Gomes as the full-back burst into the right side of the box, and Gerrard stepped up to fire the ball past the Spurs keeper.
Tottenham looked to respond straight away, with Defoe's shot on the turn blocked by Carragher.
The defender was then booked for a foul on the striker as the home side pressed again.
It proved a costly free-kick to concede, as from it, Spurs regained the lead on 59 minutes.
Modric, from the right, floated the ball over through a crowded penalty area, where Bassong got up to head into the corner and mark his debut in style.
On 67 minutes, Liverpool replaced Babel with Benayoun as Benitez opted for `Plan B', while Spurs sent on summer signing Peter Crouch for Keane.
Liverpool felt they should have had a penalty when substitute Andriy Voronin went down following a shoulder challenge by Assou-Ekotto - but this time, referee Phil Dowd was not interested.
Tempers frayed on the Liverpool bench, with assistant boss Sammy Lee sent to the stands for continued protests.