Armstrong came into the professional game back in 1989 when signing professional terms with Welsh side Wrexham.
Earned himself a reputation as a very promising youngster, netting regularly as a teenager. Millwall saw the potential and in the striker and signed him to help fill the void left by Teddy Sheringham's move to Nottingham Forest.
Made a huge impact at Millwall before - along with a lot of other fine players - he was sold by the Lions. After just 12 months at the Den he made the short move across London to Crystal Palace.
Enjoyed a fine time at Selhurst Park, but after three seasons he would move to his third London club, signing for Tottenham Hotspur for £4.5million. This time he would play with Sheringham rather than replace him.
Sometimes brilliant and sometimes infuriating, Armstrong on form is explosively fast and a seemingly effortless finisher with plenty of verve to his play.
Off it, he can look awkward and struggles to find his range, and went through some difficult patches at White Hart Lane during which sections of the crowd have turned against him.
Struggled badly with injuries over the last few seasons with Spurs, playing his last game for the club in December 2000. Was released at the end of his contract in the summer of 2002, mainly due to his fitness problems.
Armstrong played 193 games and scored 62 goals during his time at the north London club.
At one stage it looked as though Armstrong would struggle to win a deal elsewhere, but towards the end of August 2002 he signed for Bolton Wanderers, penning a short-term deal.
Trotters boss Sam Allardyce said: 'I am absolutely delighted to be bringing Chris here. He is a highly experienced player with a marvellous track record of scoring goals in the top flight.
'At the moment he is about six to eight weeks behind the rest of the squad in terms of fitness but will become an integral part of the team.'
Made his debut for the club in the embarrassing 3-1 defeat at home to Bury in the Worthington Cup in October.