He was raised by foster parents in Wales, where he began playing as an amateur goalkeeper in local leagues, before leaving school and giving up on football aged 16.
[3] The Independent sports writer Glenn Moore criticised The FA for punishing Armstrong despite not taking action against Dennis Wise and Vinnie Jones for recent violent offences, adding that cannabis was extremely unlikely to have aided his performance.
[9] After interest from FA Cup holders Everton, Armstrong joined Tottenham Hotspur for a fee of £4.5 million in June 1995, replacing Bayern Munich-bound Jürgen Klinsmann.
[8] With the funds coming from a new kit deal and the sales of Klinsmann, Gica Popescu and Ilie Dumitrescu, this made him both Tottenham's most expensive signing,[8] until Les Ferdinand for £6 million in 1997.
He totalled 22 goals (15 league) in his first season, including the winner in the North London derby against Arsenal on 18 November at White Hart Lane.
[12] On 28 December 1998, Armstrong scored a late hat-trick in a 4–1 home win over Everton, and when he was substituted at the end of the game his teammate David Ginola got in his way to bow down to him.
[13] He scored five times in their League Cup run that season, including two in a 3–1 win over Manchester United in the quarter-finals, but was unused in the final at Wembley Stadium which Spurs won over Leicester City.
[15] On 28 August 2002, Armstrong signed for Bolton Wanderers in a deal that would see him earn a low wage until his first-team debut, estimated at two months away due to fitness.
[18] Towards the start of his professional career, Armstrong was tracked by Wales, and was called up by Nigeria ahead of the 1994 FIFA World Cup, but turned them down in hope of representing England.
[5] Republic of Ireland managers Jack Charlton and Mick McCarthy also tried to enlist Armstrong in the late 1990s; he later revealed that his Tottenham contract said that he could only play for England to avoid limits on foreign players in European fixtures.