Having already taken on the Rossoneri's neighbours Inter in the group stage Spurs were looking to strengthen their European profile which had already blossomed under the guidance of Rednapp this season.
Rednapp as a manager cannot be faulted as far as I am concerned, from bringing such talents as Joe Cole, Frank Lampard and England captain Rio Ferdinand whilst at the helm at West Ham, to guiding a very average Portsmouth side to F.A cup glory in his relatively short time there.
Rednapp had never hidden the desire to manage a top four side but the opportunity never arose, so as a sign of the measure of the man, Rednapp decided that he would take over the reigns of a side outside the 'big four' and turn them into one himself.
He was given this chance with Tottenham Hotspur, but this was no ready-made blueprint however as when Harry took charge Spurs were languishing bottom of the Premiership and only had two points from their opening eight games.Within two weeks he had already made his mark pulling Spurs out of the relegation zone and from there the only way has been up.
The first full campaign with Harry saw Tottenham break the mold of the 'big four' and finished in fourth position and in turn putting the club into the Champions League for the first time, and this is where he has really made his mark.
Tottenham are currently (17/02/2011) sitting fourth once again with twelve games to go and they are only ten points off of leaders Manchester United. This alone shows the improvement that he single-handidly has given the Spurs faithful, a harem of fans that truly deserve to watch football being played at the highest possible level, and to add to that, they are more than holding their own.
It started worryingly for the London side though as they were guilty of naivety against minnows Young Boys, losing 3-2 away, but their brilliant home form see them progress to the competition proper.
From there they faced games against Inter Milan, Werder Bremen and FC Twente, Inter were reigning champions and not many people gave Spurs, in their maiden season, much hope to qualify.
Whether it was the 'unknown entity' factor or not, Tottenham repaid their terrific support by finishing top of their group against all the odds, they progressed to the last sixteen to face AC Milan, one of the true giants of European football.
The first leg of this knock-out round was played this week and it didn't disappoint anyone, whether you are a Tottenham fan, neutral, or hater, they put in a performance that ranks right up there with the best. They silenced the hostile crowd in the San Siro but playing some breathtaking football at times, they pressed the seven time winners and four times runner ups back into their shell from the off, frustrating the home side and showing the footballing world that they are in the competition not just to make up the numbers but to progress as far as possible, and on this form, with the magician Harry pulling the strings behind the scenes, who can say how far he might take them.
This performance gave benchmarks to Tottenhams fantastic run so far in the competition, a true yard-stick to measure the opening jitters they undoubtedly encountered at Young Boys on the first match day.
It showed just how far they have matured under the man-management of Rednapp, he is clearly top of the tree when it comes to getting the most out of his players, as Palacios and Sandro controlled the centre of midfield against World Cup winner Gennaro Gattuso, and his back four made Robinho and Ibrahimovic look like two lost puppies.
Yes it is only half time in the tie but I can really see Spurs making not just the quarter finals but I think they are well capable of reaching the final four. If this turns out to be the case, then who knows where Harry will lead them.....
1901-FA Cup Winners
1921-FA Cup Winners
1961-FA Cup Winners
1981-FA Cup Winners
1991-FA Cup Winners
1971-League Cup Winners
So as this season's showpiece final will of course be settled in 2011, are we looking and watching yet another piece in Tottenham's history where their victories see them add another trophy to the list of '1'??????
English teams are so good in Europe....why???? Here's what I think....http://hubpages.com/hub/English-Clubs-In-Europe