Samways began his football career in
Tottenham Hotspur's youth system. He won the
FA Cup with Tottenham in
1991, and helped them reach the semi-finals of the competition in 1993. He was a regular player in the side which reached the quarter-finals of the
European Cup Winners' Cup during the
1991–92 season. Samways was put on the transfer list in the 1992 close season, but was taken off it at his own request and spent a further two seasons at
White Hart Lane. He joined
Everton in 1994, and was part of the Everton squad that reached the
1995 FA Cup Final, but Samways was left out of the team for the final itself. He did however score the only goal of the
1995 Charity Shield to defeat league champions
Blackburn Rovers. In the
1995–96 season, he spent time on loan at
Division One sides
Wolverhampton Wanderers and
Birmingham City. Unable to settle at Everton, Samways enjoyed a degree of success in Spain with
UD Las Palmas during the late 1990s and early 2000s, where he was
team captain and played a key role in the
Canary Islands side. In 2002–03, he played ten league games with
Sevilla FC, becoming the first Englishman to play in the Sevilla derby against
Real Betis. He then returned to England, where he spent the
2003–04 season with
Walsall in Division One. He then went back to Spain, joining lower league side
Algeciras CF, and retired in 2005, aged 36. ==Coaching career==