Harry Redknapp will get the chance to mark another defining moment in his long managerial career when he leads Tottenham into the UEFA Champions League for the first time in the club's history on Tuesday.
Redknapp took over Spurs during last season and led them to an impressive fourth place finish in the Premier League. "At least I can always say to the grandchildren, 'We finished fourth one year when I was at Tottenham, we got into the Champions League'," Redknapp said.
Now Redknapp, who has also managed Bournemouth, West Ham, Portsmouth (twice), and Southampton in a 27-year career, must steer Spurs through a two-leg play-off against Swiss side Young Boys, who host the first leg in Berne, in a bid to join the lucrative group stages. Going on their performance in a goalless draw against Manchester City on Saturday, when only City goalkeeper Joe Hart denied Spurs a win, Redknapp's task looks to be achievable.
Young Boys were ousted 5-2 on aggregate by Red Star Belgrade in the 2004/05 edition's second qualifying round, and were beaten 5-1 by Real Madrid in the old European Cup first round in 1986/87. Tuesday's tie, and more so the return leg next week, will have special significance for Young Boys defender Scott Sutter, who grew up in London and used to have a season ticket for White Hart Lane.
"It was amazing for me when I was watching the draw with my dad and the first two names out were us and Tottenham," Sutter told uefa.com. "I jumped up and punched the air. The club I support and once had a season ticket; I can finally play at White Hart Lane. It couldn't get any better."
Ten group place spots will be up for grabs over Tuesday and Wednesday's ties with the second-leg matches to take place next week. Also in action on Tuesday will be Ajax, Norwegian hopefuls Rosenborg, Czech side Sparta Prague, and 2008 UEFA Cup winners Zenit St Petersburg.
Former European champions Ajax face Dynamo Kiev, who, with Andriy Shevchenko on board, are bidding for their fifth group stage campaign in a row. Shevchenko has direct experience of Ajax, having twice scored a game-winning goal against the Dutch league runners-up when he played for AC Milan.
Norwegian champions Rosenborg host Danish counterparts Copenhagen as both sides bid to join the group stages after several years away. Sparta Prague have qualified for the group stages seven times but are looking to return for the first time since 2005 having fallen at the last qualifying hurdle in the past three seasons. They host MSK Zilina from Slovakia.
Zenit are the only unbeaten team after 16 games in the Russian league but manager Luciano Spalletti has urged caution against an Auxerre side which finished third in the French league last season. "We need to keep ourselves concentrated throughout the match," said Spalletti, who will be missing Croatian defender Ivica Krizanac through injury. "Auxerre are very serious opponents and if we want to win we will need to be on top form."