Pavel Pogrebnyak headed the Royals into a shock lead on four minutes, however Dawson nodded home from a Gylfi Sigurdsson corner kick three minutes later to level the scores with his first goal at White Hart Lane in four years.
Spurs created numerous chances in the second half and converted two of them. Adebayor scored his first home goal of the season with a thumping header following a deep cross from Aaron Lennon shortly after the restart.
Dempsey then sealed the win with a deflected long-range effort, which marked his first home goal since joining Spurs from London rivals Fulham.
Below, Sports Mole takes an in-depth look at the action in North London.
On target 11
On target 2
Was the result fair?
Yes, it was. As the stats reflect, Spurs were dominant over the course of 90 minutes. They could easily have added to their tally too. However, at 2-1, the Royals had six-minute spell where they almost equalised on three occasions.
7/10. Spurs attacked relentlessly and peppered the visitors' goal. However, their final ball frequently let them down and they seemed to lack a little creativity in the final third, shooting from distance rather than coming up with the killer pass. Judging by today's performance, Luka Modric and Rafael van der Vaart are still sorely missed at White Hart Lane.
6/10. The Royals defended reasonably well and denied the hosts time and space inside the penalty area, forcing Spurs to try their luck from long range. Also, as mentioned above, Brian McDermott's men came close to levelling three times during the second half. First, Pogrebnyak was denied by Hugo Lloris, before Kyle Walker produced a superb last-ditch tackle to halt Jimmy Kebe, who was clean through on goal. Dawson then cleared an Alex Pearce effort off the line.
Sports Mole's man of the match
Aaron Lennon: The absence of Gareth Bale was the major talking point ahead of the match, but Lennon produced a performance of the highest order to ensure that the Welshman was not missed. The England winger terrorised Ian Harte all afternoon and provided a perfect cross to set up Adebayor's goal.
Biggest gaffe of the match
All in all, it was a pretty gaffe-free affair. Sandro's shooting was pretty awful, though, and the Brazilian was off target with five of his six efforts, one of which ballooned horribly wide.
Howard Webb was outstanding. In fact, he finished a close second behind Lennon for man of the match. The former policeman ruled with supreme authority. He received no complaints from either set of players and must be commended for the way he allowed the advantage to be played on numerous occasions. No bookings were shown.
Spurs: Tottenham host League One Coventry in the FA Cup on Saturday. The Londoners have won their last three matches against the Sky Blues.
Reading: The Royals are also in action against third-tier opposition. They travel to the Broadfield Stadium for their first ever match against Crawley Town.