Stakes high as Milan and Ajax meet

A place in the last 16 of the UEFA Champions League is up for grabs at San Siro where second-placed AC Milan are looking to hold off Group H rivals AFC Ajax.

Christian Poulsen and Mario Balotelli contest possession at the Amsterdam ArenA
Christian Poulsen and Mario Balotelli contest possession at the Amsterdam ArenA ©Getty Images

A place in the last 16 of the UEFA Champions League is at stake as AFC Ajax visit AC Milan on matchday six. 

• Milan's 3-0 win at Celtic FC last time out ensured they stayed a point clear of AFC Ajax in Group H, despite the Dutch champions' impressive 2-1 defeat of Barcelona, meaning the Rossoneri only need avoid defeat to ensure their progression.

• Ajax must win and will be hoping that lightning will strike twice for coach Frank de Boer who oversaw a victory at San Siro in his first match at the helm of the Amsterdam club in December 2010, at the end of another UEFA Champions League group stage campaign.

• Ajax came close to beating Milan in Amsterdam on matchday two, taking a 90th-minute lead through Stefano Denswil only for Mario Balotelli to equalise with a penalty in the fourth minute of stoppage time.

Previous meetings
• In the 2010/11 group stage the clubs met in Amsterdam on matchday two, with Milan's Zlatan Ibrahimović (37) scoring against his old club to cancel out Mounir El Hamdaoui's goal (27) in a 1-1 draw.

• Demy de Zeeuw (57) and Toby Alderweireld (66) gave Ajax a 2-0 win in the return to secure the visitors third place in the group against a Milan side already assured of progress. That contest on 8 December 2010 marked De Boer's first game in caretaker charge after Martin Jol's departure.

• Ajax's sole survivors from those 2010/11 ties are Eyong Enoh and Siem de Jong while only Marco Amelia, Ignazio Abate and Daniele Bonera were involved for Milan.

• Milan overcame Ajax in the 2002/03 UEFA Champions League quarter-finals after drawing 0-0 in Amsterdam then winning 3-2 at home through an added-time Jon Dahl Tomasson goal. The following season the teams met in the group stage and Milan won both matches 1-0, Kaká involved each time.

• The clubs' first encounter was in the 1968/69 European Champion Clubs' Cup final, Milan winning 4-1 in Madrid. Ajax gained revenge in 1994/95 when a team including De Boer and captained by Daley Blind's father Danny beat Milan both home and away in the group stage and then a third time in the final. Patrick Kluivert, later a Milan player, scored the only goal in Vienna.

• Ajax overwhelmed Milan in the 1973/74 UEFA Super Cup, overturning a 1-0 first-leg loss with a 6-0 home victory.

Match background
• Massimo Allegri's Milan are undefeated in three European home matches in 2013/14 and have already got the better of one Eredivisie club at San Siro this term, beating PSV Eindhoven 3-0 in the UEFA Champions League play-offs. Kevin-Prince Boateng (2) and Balotelli scored the goals that completed a 4-1 aggregate success.

• Milan's overall home record against Dutch opposition is W7 D1 L3.

• Beaten at Barcelona and Celtic this season, Ajax have not won any of their last six away fixtures in the UEFA Champions League, a winless sequence stretching back to 18 October 2011 and a 2-0 success at GNK Dinamo Zagreb.

• Ajax are unbeaten in their last three matches in Italy, however. Their overall record away to Serie A opposition is W4 D5 L10.

• Ajax have contested three other European Cup finals against Italian clubs, defeating FC Internazionale Milano in 1971/72 and Juventus in 1972/73, but losing to Juventus in 1995/96. They also faced Torino FC in the 1991/92 UEFA Cup final, prevailing on away goals.

Team ties
• As a player De Boer featured in Ajax's 1992 and 1995 triumphs against Torino and Milan respectively but also their 1996 loss to Juventus. He also lost a 1996/97 UEFA Champions League semi-final against Juventus with Ajax and a UEFA EURO 2000 semi-final against Italy with the Netherlands, when he missed a penalty in normal time and another in the shoot-out.

• De Boer was in the FC Barcelona side that failed to qualify from the 2000/01 UEFA Champions League first group stage after losing 2-0 at home to Milan and drawing 3-3 away.

• Bojan Krkić made 19 Serie A appearances on loan at Milan last season, scoring three goals. At Roma in 2011/12 he played 33 times in Serie A and scored seven goals, incuding one in Roma's 3-2 home loss to Milan in October 2011, and also featured in their 2-1 loss at San Siro.

• Christian Poulsen played for Juventus between 2008 and 2010, recording one draw and two defeats against Milan in Serie A. With Sevilla FC he lost the 2007 UEFA Super Cup 3-1 against Milan while as an FC Schalke 04 player he faced the Rossoneri in the 2005/06 UEFA Champions League group stage, appearing in a 2-2 home draw and scoring in a 3-2 away defeat that eliminated the German club.

• Blind made his Netherlands debut on 6 February this year in a 1-1 friendly draw with Italy at the Amsterdam ArenA, with Ricardo van Rhijn appearing as a substitute. Riccardo Montolivo, Abate, El Shaarawy and Balotelli lined up for the opposition.

• Blind, Van Rhijn and Mike van der Hoorn played in the Netherlands' 1-0 loss to Italy in June's UEFA European Under-21 Championship semi-finals. Riccardo Saponara was an unused Azzurrini substitute.

• Kaká helped Real Madrid beat Ajax home and away in each of the last two seasons. After featuring in a 4-1 group win in Amsterdam on 3 October last year, he scored in an identical victory at the Santiago Bernabéu. Kaká had found the net against Ajax in a 3-0 home success on matchday two of the 2011/12 season before featuring again as Madrid triumphed 3-0 away.

• The Amsterdam-born Nigel de Jong and Urby Emanuelson both began their careers at Ajax; the former made 96 Eredivisie appearances between 2002 and 2006, and the latter 172 from 2004 to 2011. Emanuelson spent the second half of last term on loan at Fulham FC with Enoh.

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