Mourinho goes for glory in the Champions League with Inter Milan, while Blackpool boss Holloway will take them into the Premier League with victory in the play-off final.
But despite the huge rewards on offer, the two managers will command much of the attention thanks to their ability to reel off unforgettable quotes.
Love him or hate him, Mourinho has become a cult figure on these shores for his words, while Holloway is one of the funniest managers around.
In tribute to the pair, Sportsmail's latest List is the best football manager quotes ever.
We've kept it to those who were working in Britain at the time and make no apologies for certain individuals appearing more than once.
We hope you enjoy our latest countdown and, as always, tell us your favourite quote.
50 Port Vale's John Rudge'I've been at Port Vale for 16 years. Even the Great Train Robbersdidn't get that long a sentence. Here you are manager, coach, chiefscout, chief cook and bottle washer, but I've loved every minute of it.'
Long-serving boss: John Rudge
49 Manchester United's Sir Alex Ferguson on the Premier League title race in 2003 'It's squeaky-bum time.''
The master: Sir Alex Ferguson saw his United side claim a thrilling title in 2003
48 Hamilton's Iain Munro in 1995'I'd hang myself but we can't afford the rope.'
47 Wimbledon's Joe Kinnear on his answerphone message'I'm out at the moment, but should you be the chairman of Barcelona,AC Milan or Real Madrid, I'll get straight back to you. The rest canwait.'
Crazy: Joe Kinnear in his Wimbledon days
46 West Ham's Harry Redknapp on Ron Atkinson'The only relaxed boss is Big Ron. He had me drinking pink champagne - before the match.'
Two of the great characters: Ron Atkinson and Harry Redknapp
45 St Johnstone's John McClelland'I was on a drip in a hospital bed and this player came in to seeme. I thought he was was enquiring about my health. He never even askedhow I was. All he was interested in was how he stood regarding thecontract. He'd even bought his agent in.'
44 Leeds' Howard Wilkinson'There's only two types of manager. Those who've been sacked and those who will be sacked in then future.'
The toughest of jobs: Howard Wilkinson pictured in 1993 when managing Leeds
43 Coventry's Ron Atkinson on Gordon Strachan'There's nobody fitter at his age - except maybe Raquel Welch.'
Praise indeed: Ron Atkinson and Gordon Strachan
42 Republic of Ireland's Jack Charlton on Paul McGrath 'Paul is one of the all-time greats, someone to compare to BobbyMoore. He has always been a very intimidating player. I used to tellhim: 'Just look your opponent in the face, smile at them, and you'llfrighten them to death.''
When Irish eyes are smiling: Jack Charlton with Paul McGrath during training at the 1994 World Cup
41 Newcastle's Kevin Keegan on signing Rob Lee 'I told him Newcastle was nearer to London than Middlesbrough, and he believed me.'
Famous days: Keegan bewitched football as Newcastle boss in the 1990s
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