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Master vs apprentice: 7 times managers faced off against former assistants

Carlo Ancelotti goes head-to-head with Zinedine Zidane as Bayern Munich take on Real Madrid, the latest in a long line of managers to take on a former assistant. But who’s had the upper hand?

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1. Louis van Gaal vs Jose Mourinho

The Manchester United super-managers first worked together at Barcelona, when they won two La Liga titles – Mourinho working as Van Gaal’s assistant. The Dutchman played a mentoring role, encouraging the young Portuguese to go into management.

There are echoes of his prickly man management style in the way Mourinho deals with his players. Admittedly, he’s yet to drop his trousers to make a point during a training session. As far as we know, anyway - is this why Luke Shaw looks so traumatised?

He trains to win. I train to play beautiful football and win. My way is more difficult

- Louis van Gaal

Mourinho took the best parts of the Dutchman’s approach, but with a more pragmatic style. As the Dutchman once observed: “He trains to win. I train to play beautiful football and win. My way is more difficult.”

Van Gaal had cause to rue his creation, as the pair faced off in opposing dugouts for the first time in the 2010 Champions League final. Van Gaal’s Bayern Munich were slight favourites. Mourinho’s Inter were the poorer team on paper, but had stunned Barcelona in the semi-finals over two legs to reach the final in Madrid. What followed was a classic counter-attacking performance, Inter winning 2-0 with goals from Diego Milito.

Jose Mourinho

Mourinho got the upper hand over Van Gaal in 2010

Mourinho’s Chelsea also got the better of the pair’s two Premier League meetings: a heated 1-1 draw at Old Trafford followed by a 1-0 Chelsea win at Stamford Bridge.

Verdict: A comfortable victory for Mourinho, the devious apprentice, with two wins and one draw from three meetings.

2. Jose Mourinho vs Andre Villas-Boas

As a semi-permanent scowl seemed to settle on Mourinho’s once youthful visage, a new Portuguese manager seemed set to take his place as the next bright young thing. Andre Villas-Boas was Mourinho’s assistant at Porto, Chelsea and Inter before they parted ways.

You fall in love with him and he becomes your idol

- Andre Villas-Boas

“In my formative moments working with Jose was the best time of my life – I was able to lean to many things and working with him takes you to another level," said Villas-Boas. “You fall in love with him and he becomes your idol."

Touching. Yet their relationship soured after AVB elected to launch his own managerial career - first at Academica, then following in Mourinho’s footsteps at Porto (where he won a treble in his first season in charge) and Chelsea. They’ve faced off just once, a 1-1 Premier League draw at White Hart Lane in September 2013 during AVB’s time at Spurs. He was sacked two months later.

Andre Villas-Boas

Andre Villas-Boas gurns in Mourinho's shadow

Verdict: Honours even, although with AVB managing Shanghai SIPG after a spell at Zenit Saint Petersburg, it’s clear that the master had the last laugh here. Mourinho also has a winning record (P1, W1) against Aitor Karanka, who was his assistant for three years at Real Madrid.

3. Alex Ferguson vs Steve McClaren

Manchester United chairman Martin Edwards introduced their new assistant manager as “Steve McClaridge” when he joined from Derby early in 1999, but he turned from unknown into one of the most coveted managers in the game after helping Alex Ferguson to three straight Premier League titles, and of course the treble. He’d initially hoped to succeed Ferguson when the Scot initially announced his retirement in 2001 – interesting alternative reality for you to imagine, there – but opted to join Middlesbrough after Fergie changed his mind.

Alex Ferguson

Fergie and Steve McClaridge... sorry, McClaren at an unidentified location

Sir Ferg had a habit of crushing teams managed by his former players – Steve Bruce was a constant victim – but McClaren’s record actually stands up pretty well. They faced each other 12 times in a five-year period, with five wins each and two draws. Boro even dumped United out of the FA Cup in the fourth round in 2002, while a 4-1 win at the Riverside with goals from Gaizka Mendieta and Yakubu also stands out. 

Verdict: Dead level, but a moral victory for the much-maligned McClaren: not many managers have an equal head-to-head record with Alex Ferguson.

4. Brian Clough vs Peter Taylor

Together, they pulled off some of the greatest achievements in the history of English football. First at Derby County, then with Nottingham Forest – but their relationship soured. Taylor retired in 1982, leaving Clough at Forest, but returned to football in November of that year as manager of second division Derby.

The pair ignored each other completely when their sides were drawn together in the FA Cup third round in January. Former Forest star Archie Gemmill sealed a 2-0 win for the Rams, and Forest’s players said they’d never seen Clough as angry as he was after the game.

If his car broke down and I saw him thumbing a lift, I wouldn't pick him up, I'd run him over

- Brian Clough

In June 1983, they fell out completely when Taylor signed John Robertson from Forest without telling Clough. Ol’ Big Head attacked his former assistant in a newspaper column, calling him a rattlesnake. ”We pass each other on the A52 going to work on most days of the week,” he wrote. “But if his car broke down and I saw him thumbing a lift, I wouldn't pick him up, I'd run him over"

The pair never spoke again, to Clough’s great regret. Four years after Taylor’s sudden death in 1990, Clough dedicated his autobiography to him, writing: “To Peter. Still miss you badly. You once said: ‘When you get shot of me there won't be as much laughter in your life.’ You were right.”

Verdict: Taylor, who deserved a better title than just ‘assistant’ edges it, but in truth they were always better together.

Brian Clough

Clough and Taylor: just the two European Cup wins together