The last time a Liverpool manager won their first game in charge, the Spice Girls sat at the top of the UK charts and Tony Blair still had the youthful vibrance to charm the public.
Gerard Houllier went on to win an FA Cup and a UEFA Cup title in his tenure, but never quite took his team to the heights that some thought they were capable of.
The normal one
Jurgen Klopp faces a similar challenge with his current Liverpool squad, many of whom will be negatively affected by the selling mentality of the Anfield club in recent years. But he is hoping for grander rewards than minor trophies.
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The trouble lies in making progress after a legacy of letting your best players leave for a profit. The German inherits a decidedly average team with a wealth of injury problems who could not sustain two good years in a row under stable leadership.
Tottenham Hotspur, on the other hand, are hoping for something of a mini-revival to round off the beginning of the season.
Mauricio Pochettino has also suffered from a lack of control over transfer policy and losing big players, but after losing the opening game of the season Spurs are yet to feel the pain of defeat in the Premier League since then.
The victor of the match-up will undoubtedly gain momentum for the rest of the season, and likely edge out the loser come the end of the current campaign when it comes to qualifying for European competition.
A draw would see both teams remain in limbo for the foreseeable future, struggling to compete with the top four teams for longevity and forever destined to have a 'normal' season.
Liverpool fans: Would a win at White Hart Lane get your season back on track? Give YOUR opinion in the comment box below!