Clarence Seedorf and Diego Simeone will face off for the first time as coaches when AC Milan and Club Atlético de Madrid meet in the UEFA Champions League round of 16 – also the first encounter between the teams – but the pair were well acquainted as players. UEFA.com runs through their memorable duels.

14 June 1997 – Real Madrid 3-1 Club Atlético de Madrid

Seedorf and Simeone locked horns for the first time in the penultimate matchday of 1996/97, with Simeone's Atlético looking to dent Liga-leading Madrid's title ambitions. Unbowed by pressure from second-placed FC Barcelona, the Merengues blew away their rivals with a dynamic display, and it was Seedorf's clever ball that sent Predrag Mijatović through to seal a fine win. Madrid duly lifted their 27th Spanish championship.

19 September 1998 – Real Madrid CF 2-0 FC Internazionale Milano

Seedorf was an unused substitute for the Netherlands team that beat Simeone's Argentina 2-1 in the 1998 FIFA World Cup quarter-finals, but the pair did meet twice the following season, with the UEFA Champions League group stage providing the backdrop. Simeone was by now at Inter, with whom he had captured the UEFA Cup in 1997/98, yet it was the same story for the Argentinian against Seedorf. The Dutch midfielder pounced in the final minute to seal a 2-0 home success for holders Madrid.

Seedorf in action for Real Madrid ©Getty Images

25 November 1998 – FC Internazionale Milano 3-1 Real Madrid CF

Seedorf found the net again in the trip to San Siro two months later, cancelling out Iván Zamorano's opener with a powerful near-post header. This time, though, Simeone had the last laugh as Roberto Baggio struck twice in the last four minutes to earn a 3-1 Inter victory. Both sides progressed from Group C before suffering quarter-final exits.

11 March 2000 – SS Lazio 2-2 FC Internazionale Milano

Simeone moved to Lazio in 1999, meaning he just missed out on playing alongside Seedorf when the Dutchman joined the Nerazzurri that December. Seedorf enjoyed the better of their first Serie A contest, chalking up an assist after recovering an overhit cross and picking out Luigi Di Biagio for Inter's second. Simeone had been replaced by Fabrizio Ravanelli after half-time and watched as Lazio snatched a point with two late goals. The Biancoceleste went on to beat Juventus to the Scudetto by a single point.

Simeone (C) with the Coppa Italia ©Getty Images

12 April/18 May 2000 – SS Lazio 2-1 FC Internazionale Milano (agg)

A month later, the duo went head to head with the Coppa Italia at stake. Lazio prevailed 2-1 in the two-legged final, with all three goals coming in the first instalment at the Stadio Olimpico. Seedorf and Simeone both registered in an entertaining opening contest; the latter bravely diving to head in what proved to be the decisive goal after Seedorf's close-range effort had been cancelled out by Pavel Nedvěd.

8 September 2000 – SS Lazio 4-3 FC Internazionale Milano

Seeking vengeance for their Coppa Italia defeat, Seedorf's Nerazzurri again came away from the capital empty-handed as Lazio's annus mirabilis was further gilded by the addition of the Italian Super Cup. A motivated Inter broke the deadlock early on, yet Simone's team soon took control and stormed into a 3-1 lead – only a stunning save from Inter keeper Marco Ballotta prevented the Argentinian midfielder getting in on the act. A creative Seedorf helped Inter battle back, but in vain.

21 January 2001 – SS Lazio 2-0 FC Internazionale Milano

Lazio were already a goal to the good when Simeone was introduced from the bench after 56 minutes. Sent on to stiffen up the midfield and keep Seedorf, six years his junior, in check, Simeone did not disappoint. Lazio ended the season third, 18 points and two places above Inter.

5 May 2002 – SS Lazio 4-2 FC Internazionale Milano

Seedorf looked on from the bench as Inter suffered a 4-2 last-day reverse at Lazio that cost the Milan club the Scudetto. The Nerazzurri had led Juve by six points at the summit with five games to go, but an end-of-season collapse – culminating in this loss – left them cursing their luck. Level at 2-2 after half-time, the 32-year-old Simeone powerfully headed the fifth goal that swung momentum Lazio's way. His side snatched a UEFA Cup spot at the death, while Inter saw Juve lift the Scudetto. It was Seedorf's last match in black and blue before joining neighbours AC Milan.