Pep Guardiola, Carlo Ancelotti and Jose Mourinho have all twice won Europe's greatest prize and will lead Bayern Munich, Real Madrid and Chelsea respectively into the last four first legs on Tuesday and Wednesday.
All three bosses have the chance to become the best the tournament has seen in its 22-year history, with a third triumph enough for them to surpass the record of the Champions League's most successful coach - Sir Alex Ferguson.
The Manchester United icon reached the final on four occasions, winning two of those in 1999 and 2008, while his record of seven semi-finals has only this season been bettered by Mourinho. His tally of quarter-final appearances (12) remains unsurpassed.
|CHAMPIONS LEAGUE'S ALL-TIME TOP COACHES
|Sir Alex Ferguson||2||4||6||12|
|Vicente del Bosque||2||2||4||4|
|Louis van Gaal||1||3||5||6|
In the above table, Goal has ranked the top coaches from the Champions League era (beginning in 1992-93) in an Olympics-style system. Bosses are assessed initially based on the number of tournament wins, followed by final appearances, then semi-final outings, and lastly quarter-final spots.
Ferguson remains the Champions League's most successful head coach, but with Guardiola, Mourinho and Ancelotti all on the cusp of a third title, one of the trio could move to the top of the table by the end of this season.
Guardiola twice won the prize with Barcelona, in 2009 and 2011, Ancelotti did the same with AC Milan in 2003 and 2007 - losing a final in between in 2005 - while Mourinho emerged victorious with Porto in 2004 and Inter in 2010.
The top 10 consists of three Italians, two Spaniards, two Germans, a Scot, Dutchman and Portuguese. Rafa Benitez just misses out on a place on the list with one trophy and two finals. Arsenal manager Arsene Wenger also fails to make the cut with just one unsuccessful final appearance and two semi final outings during his career.
Only Liverpool icon Bob Paisely has lifted Europe's top prize three times, but that was before the Champions League era.
Mourinho already holds the record as the first head coach to reach the last four with four different clubs (Porto, Inter, Real Madrid and Chelsea) but will he be the first man to clinch his third Champions League crown?