It was the 18-year-old from Toronto who got on the scoreboard in a losing cause as Tottenham defeated Toronto 3-2 in a soccer friendly Wednesday on the strength of an 85th-minute goal by Andros Townsend.
Andrew Wiedeman and Hamilton had scored second-half goals to pull the home side even before a sellout crowd of 22,591 on a warm evening at BMO Field. Lewis Holtby set the table for the Spurs winner, driving towards goal before finding Townsend who curled a shot past Quillan Roberts, another homegrown teenager.
Argentine midfielder Erik Lamela scored twice for Tottenham in the first half before Toronto shot back in a far more competitive and entertaining second after the teams combined for 17 changes at the break.
"It was a different game," Spurs manager Mauricio Pochettino said of the second half.
It was only the second pre-season game for Tottenham, with Pochettino reminding his post-game audience that "for me, it's another training session and it's game that was good for our supporters, to show our improvement."
In the first half, Toronto seemed to have one eye on its weekend league match with defending MLS champion Sporting Kansas City.
Defoe got virtually no service from his teammates and found himself having to take up the role of playmaker to get something going. The England star was substituted at halftime, one of seven changes by manager Ryan Nelsen. Veteran Dwayne De Rosario took over as captain and told his crew that change was needed.
"I just told the guys we didn't come here to spectate," De Rosario said. "This is our field, this is our home. We have to take it to them. I think we did that in the second half and we were able to put them under pressure and force them to cough up the balls where we could attack and counter-attack. We started to build confidence from that."
Said fellow second-half substitute Nick Hagglund: "We came in with the mentality to really press them and make them play well. And I think when we did that, we showed that they're human, that they make mistakes, just like us."
On a night where he was on the marquee, Defoe was largely on the outside looking in.
Defoe, 31, played 362 times in two stints with Tottenham before departing for Toronto FC in January. He scored 142 goals for Spurs, fifth on the club's career scoring list. Ironically Defoe just hit No. 5 on Toronto FC's all-time MLS scoring chart with 11 goals in 14 MLS games — evidence of the franchise's past scoring woes.
He said playing Spurs was strange but enjoyable.
"I suppose when I finish football and I look back on these memories and really reflect and think 'You know what," (about) all the years at Tottenham — it's a special club with special fans. A good bunch of players. Nice people," he said.
Defoe, balancing a plate of salmon, chatted with old Tottenham friends after the match before returning to the Toronto locker-room to do his media duties.
The game was part of Defoe's transfer agreement, which also featured a marketing deal between the two clubs. It's attention that the England striker clearly wouldn't mind doing without.
"I just love playing football," he said. "I always have done. I think at the age of 31 to still wake up in the morning and still enjoy training and look forward to every game, I still get the same buzz. And to me that's important."
Then again, he is making US$6.18 million this season, with the two cellphones sitting in his locker proof that he is by no means a hermit.
Spurs controlled the first 45 minutes against a makeshift Toronto lineup, controlling possession for long stretches and then dispossessing Toronto when the home side got it back. Tottenham outshot Toronto 10-0 (3-0 in shots on target) in the first 45 minutes.
Toronto, with six Canadians on the field, had a much stronger second half. Spurs again had more shots (10-5) but the home side had more on target (3-2).
Wiedeman cut the deficit to 2-1 in the 65th minute. Rookie winger Daniel Lovitz, one of the bright spots for Toronto, made the goal by pouncing on a Tottenham turnover and driving towards goal before opening up the defence with a through ball to Wiedeman.
Hamilton tied it up in the 73rd minute, capping off passes from Hagglund and Wiedeman with a clinical left-footed shot from the edge of the penalty box. It was the first goal for Toronto for Hamilton, who has been playing for the Wilmington Hammerheads of the USL Pro league this season.
"He's someone who impressed me from Day 1," said Defoe. "Strong, has a nice left foot and he can score goals."
Nelsen said the loan to Wilmington has done wonders.
"We've seen a change ... He's acting like man not a boy and he played like it today."
Hamilton was humble afterwards when asked about his performance. But he clearly believes he has more goals in him.
"I hope I have a lot more and a lot bigger ones. It was just a friendly but it was great to score my first goal for Toronto," he said.
Lamela, who had one goal in a disappointing injury-shortened 2013-14 season, was one of 10 players withdrawn at halftime by Tottenham. The 22-year-old former Roma player reportedly cost Spurs a club-record 30 million pounds (C$55 million).
The game came at an inopportune time for Toronto, squeezed between league games against Houston and Sporting Kansas City and in a month packed with eight contests.
Toronto, already missing defenders Steven Caldwell and Mark Bloom and Brazilian winger Jackson through injury, essentially fielded just four regulars — defender Doneil Henry, midfielders Dominic Oduro and Collen Warner, and Defoe — in its starting 11. Goalie Joe Bendik didn't dress and star midfielder Michael Bradley did not stray from the bench.
Goalie Chris Konopka, defenders Jeremy Hall and Ashtone Morgan and midfielder Lovitz have a combined two MLS starts between them this season.
Konopka's MLS log reads two games in five seasons with four teams and he looked rusty. The 29-year-old was replaced by 19-year-old Roberts, who has also been playing for Wilmington.
Roberts, who has yet to see MLS action but has now played against Roma, Liverpool and Tottenham, made several good saves.
Lamela opened the scoring in the 16th minute on a pass from Roberto Soldado and a nice dummy from Aaron Lennon that froze the defence. The Argentine midfielder, who showed his flair from the get-go, then beat Konopka with an angled shot into the corner.
Lamela made it 2-0 in the 40th minute from a similar spot after slick passing from Lennon and Soldado sliced open the home defence.
Spurs opened their pre-season last Saturday with a 3-3 tie with the Seattle Sounders before 55,349 at CenturyLink Field. Their North American trip wraps up with a Sunday game in Chicago against the MLS Fire.
Tottenham finished sixth in the Premier League last season with a 21-11-6 record. It kicks off this season Aug. 16 at West Ham.