16. Paul Konchesky
Konchesky became the unfortunate on-field representative of Roy Hodgson’s ill-fated tenure at Liverpool in 2010/11. The left-back had been a key part of the Fulham team that reached the Europa League final under the future England manager, but he was out of his depth at Anfield and promptly shipped off on loan to Nottingham Forest when Kenny Dalglish replaced Hodgson in January 2011.
Konchesky made even fewer league appearances (12 vs 15) for Tottenham during a loan spell in 2003. His time at White Hart Lane was uneventful, although it’s perhaps telling that Spurs opted against making an offer for his services on a permanent basis.
15. Steven Caulker
Caulker’s loan move to Liverpool in January 2016 will go down as one of the most bizarre in Premier League history. The QPR-owned defender had spent the first half of the campaign as a bit-part player at Southampton, who were perfectly happy to let him join the Reds mid-season. Caulker made just three league appearances for Jurgen Klopp’s side – up front, naturally – although it later emerged he was struggling with depression during his time on Merseyside.
Caulker’s stock was considerably higher at the start of his career. He graduated from the Tottenham academy in 2009 and was highly regarded by many at White Hart Lane, but the one-time England international played only 29 games for his first club and spent more time on loan at Yeovil, Bristol City and Swansea.
14. Christian Ziege
Ziege joined Liverpool from Middlesbrough in 2000, embarking on a frustrating single-season stint at Anfield. Although he was part of the squad which won the FA Cup, League Cup and UEFA Cup, the left-back found game time hard to come by and later admitted to having issues with manager Gerard Houllier during his time at the club. He told FFT in 2017: “I still don’t know what his problem was with me… he never talked to me.”
Ziege fared slightly better at Spurs, the club he represented between 2001 and 2004. The German helped Glenn Hoddle’s men reach the League Cup final in 2002, even scoring in the final as Tottenham lost to Blackburn. With injuries limiting his availability, Ziege was allowed to return to the Bundesliga two years later.
13. Graeme Souness
Souness is heavily associated with Liverpool and also had a successful time at Middlesbrough, but those aren’t the only English clubs he represented during his time south of the border. Indeed, Tottenham were the Scot’s first professional club, although he only made a single first-team appearance for the Lilywhites before joining Boro in 1972.
12. Oyvind Leonhardsen
The Norway international was an integral part of the Wimbledon side which reached the semi-finals of the FA Cup and League Cup in 1996/97, prompting Liverpool to snap him up the following summer. He was initially a regular in Roy Evans’s starting XI, scoring six goals in 36 Premier League appearances in his debut campaign, but Leonhardsen fell out of favour when Gerard Houllier arrived in 1998.
A hard-working, industrious player, the midfielder spent three years at Spurs between 1999 and 2002. He wasn’t always a starter under either George Graham or Glenn Hoddle, but was a useful squad player throughout his time in north London.
11. Robbie Keane
Keane’s move from Tottenham to Liverpool in 2008 was acrimonious and led to Spurs filing a complaint to the Premier League about the Reds’ conduct. The Irishman was back at White Hart Lane a few months later, though; Keane scored five goals in 19 Premier League matches for Rafael Benitez’s men, but the Spanish manager let him to return to north London in the January window.
Ex-Leeds striker Keane had netted 107 goals for Tottenham the first time around, becoming a fans’ favourite and defender’s nightmare soon after joining the club midway through the 2002/03 season. His strike rate wasn’t quite as good post-Liverpool – he struck 15 times in 52 games – but only 10 players have scored more goals for Spurs.
10. Brad Friedel
Newcastle, not Liverpool, were Friedel’s first English employers, although the American glovesman didn’t make a single league appearance for the Magpies during a loan spell in 1994. He arrived at Anfield three years later, but work permit issues delayed his debut until 1998. Although Friedel turned in a handful of excellent performances for the Reds, he spent much of his Liverpool career behind David James – and, later, Sander Westerveld – in the pecking order.
9. Paul Walsh
Walsh’s three-and-a-half years at Liverpool were marred by injury, but the forward still managed to rack up over 100 appearances for the Reds between 1984 and 1988. The former Charlton and Luton man scored 37 goals during that time, winning one league title and finishing as a runner-up in the European Cup, League Cup, Charity Shield, European Super Cup and First Division (twice).
Walsh added an FA Cup winner’s medal to his collection while at Spurs, who triumphed under Terry Venables in 1991. His White Hart Lane career didn’t get off to the best of starts – Walsh later admitted he was a “ring leader” in the capital club’s drinking culture – and although he improved as time went on, the attacker failed to nail down a regular spot in the starting XI throughout his employment in north London.
8. Paul Stewart
Stewart was converted into a midfielder at Tottenham having largely been deployed as a striker at previous clubs Blackpool and Manchester City. He played virtually whenever fit during his four seasons in north London, making a total of 172 appearances and chipping in with 37 goals, two of which came in the victorious FA Cup campaign of 1990/91.
7. Neil Ruddock
Ruddock began his career at Millwall, but his maiden professional appearance came in a Tottenham shirt in 1986. It was a debut to forget for the youngster, who broke his leg – against Liverpool, incidentally – and was immediately ruled out for several months. The defender played only eight more league games for Spurs in that spell, but he returned to White Hart Lane for the 1992/93 campaign and was virtually ever-present as Tottenham finished eighth.
The following summer Ruddock joined Liverpool, for whom he averaged 23 league outings per season in a five-year spell. The centre-back was part of the infamous Spice Boys side marshalled by Roy Evans, but he did win the League Cup in 1995 and was generally a solid – if far from spectacular – presence in the heart of the defence.
6. Danny Murphy
After four formative years in Crewe’s first team, Murphy was signed by boyhood club Liverpool for £1.25m in 1997. It took a while for the midfielder to break into the starting XI at Anfield – he was loaned back to Crewe during his second season – but Murphy went on to become a key player for the Reds, for whom he made 246 appearances, scored 44 goals and won four major honours.
5. Peter Crouch
Crouch began his career at Tottenham in the late 1990s, but he struggled to break into the first team and was sold to QPR in 2000 after loan spells at Dulwich Hamlet and IFK Hassleholm. The striker returned to White Hart Lane nine years later, scoring 24 goals in 93 matches – including the effort against Manchester City which qualified Spurs for the Champions League.
4. Ronny Rosenthal
Rosenthal made a phenomenal start to his Liverpool career, scoring seven goals in eight league games during a loan spell in 1990. That return persuaded the Reds to make the deal permanent, but the former Standard Liege striker managed only 14 goals in 66 top-flight outings from that point onwards.
3. Nick Barmby
Hull-born Barmby began his playing career in north London, joining Tottenham after he’d left school in 1990. The attacking midfielder had to wait two years for his first-team debut, which came in a Premier League meeting with Sheffield Wednesday in August 1992. The 18-year-old Barmby soon established himself as a regular in Spurs' starting XI, and by the time of his departure for Middlesbrough in 1995 he’d played 87 games and scored 21 goals for his first club.
2. Jamie Redknapp
Redknapp made just 13 senior league appearances for first club Bournemouth between 1989 and 1991, but Liverpool saw enough in the young midfielder to bring him to Anfield for £350,000. It was an astute move, and the midfielder went on to be a regular in the Reds’ starting XI for much of the 1990s. Redknapp played 308 games for the Merseysiders in total, winning the UEFA Cup, FA Cup and two League Cups – although he was sidelined for the entire 2000/01 campaign when three of those trophies were won.
1. Ray Clemence
Goalkeeper Clemence is the only player who can legitimately be called a legend at both Liverpool and Tottenham. The England international is tied in fourth place with Emlyn Hughes on the Reds’ list of record appearance makers, having featured in 665 games between 1967 and 1981. Clemence claimed five First Division winner’s medals in those 14 years, as well as tasting success in the European Cup three times, the UEFA Cup twice, and the FA Cup and League Cup once each.
Clemence didn’t stay at Spurs for quite so long, but he still played 330 games for the north London outfit in all competitions. The shot-stopper won the FA Cup and UEFA Cup at White Hart Lane, before hanging up his gloves in 1988.
