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Man United 'still fragile' despite tough win vs. Leeds (1:25)

After Manchester United's 4-2 win over Leeds United, Frank Leboeuf wants to see more from the team. (1:45)

9:45 AM ET

The first leg of the round of 16 will be played on Wednesday and will be the start of a crucial three-month period for Manchester United. The big decisions that must be made by United's owners, the Glazer family, and recently appointed chief executive Richard Arnold will be affected by what happens between now and the end of the season.

The club that has won 13 titles since 1993 but has not won a title since 2013 needs to find a new permanent manager and sign a lot of players. There are big question marks over the futures of players with contracts which run beyond the end of this season, such as Anthony Martial and Marcus Rashford.

The 4-2 win at Leeds on Sunday gave United a four-point lead over their rivals in the race for the fourth spot in the league and their crucial objective of qualification for the playoffs.

It will be more difficult for United to attract the best manager and players they need to compete for major honours again, even though they will not be playing in the European Championship next season.

Man United got a player back.

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The manager

This is the most important issue that needs to be addressed by United and the one which will dictate what happens with every other football-related decision.

According to sources, no manager is currently seen as the preferred candidate, with the Glazers and Arnold determined to conduct a comprehensive search which will involve analyzing the strengths and weaknesses of each possible appointment, their playing style, the players they would need, as well as the prospects of persuading them to

The owners risk overcomplicating a process which will ultimately boil down to finding a world-class coach with a track record of producing teams that win and entertain.

According to sources, Luis Enrique, Mauricio Pochettino, and Eric ten Hag are all being considered. Brendan Rodgers has admirers at Old United, but his prospects are likely to have ended due to the recent slump in form ofLeicester City.

The compensation fee for hiring any of the above, plus wage demands and transfer requirements, will be a factor with whoever United appoint, so it will not simply come down to the best candidate for the job. The managerial appointment process is likely to be complex unless an outstanding candidate suddenly becomes available in the weeks ahead, because all have different approaches to the game.

Ralf Rangnick and the club have a lot of decisions to make in the coming months. Sebastian Frej/MB Media/Getty Images

New signings

Last summer, United spent just over 130 million dollars on new signings, including Jadon Sancho, Raphael Varane, andRonaldo.

At the end of the season, Jesse Lingard, Juan Mata, Paul Pogba, and Edinson Cavani will be free agents. While Mata and Lingard have been peripheral figures in recent months, their departure will leave holes to fill in the squad, but the loss of Pogba and Cavani will mean United have no option but to find an attacking centre-forward to replace both players.

With so many positions in need of reinforcement, United will have to prioritise and make smart additions to the squad rather

According to sources, West Ham is trying to sign Declan Rice, but with a likely valuation upwards of 80m, efforts will be made to find a less expensive alternative. Christopher Nkunku is being suggested as a possible replacement for Pogba in the attacking third of the pitch. Signing Harry Kane will cost at least 100 million pounds and would be the same amount of money as the second highest earner at the club, David de.

Finding players who can make the team better without breaking the bank is the key for United. In recent years, the likes of Andy Robertson, Diogo Jota, and Mohamed Salah have been signed by the Reds.

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Man United should resolve their managerial situation before chasing Christopher Nkunku according to Gab.

Contract issues

With the likes of Mata, Lingard, and Cavani all set to leave for nothing this summer, United must now plan for the future.

While United have the option of extending the majority of those contracts by a further year, decisions must be made on the final 12 months of their contracts.

With a new coach likely to want his own players, some of those named above may need to be offloaded to raise funds, especially if they make it clear that they will not sign new deals. Dalot and Fred are expected to be rewarded with new contracts, while Matic and Jones could both leave for a fee.

It has been reported that United will give a new contract to Marcus Rashford, but will he get a big pay rise and extended deal? Will he commit to a club that has failed to challenge for the top honours during his five years in the first-team? The recent form of Marcus Rashford does not justify the reward of a new contract, so that is one situation to watch closely, as he is too valuable a player to risk losing for nothing.

Whoever United appoint as their new manager will have to decide if they want to stick with the Spain international who remains one of the most naturally gifted goalkeepers in the world or if they need a more modern sweeper-keeper. A bold decision to sell De Gea could lead to significant funds being gathered for new signings and avoid the risk of the Spaniard leaving as a free agent in 2023 or, if United choose to extend by 12 months, in 2024.

Player exodus

Manchester United is ripe for clear-out. The new manager will inherit a squad that has been constructed by five different managers, from Sir Alex Ferguson through to Solskjaer, and many of those players have under-performed. With at least four out-of-contract players set to leave, can United afford to lose more? Is it possible that they have to reach the end of the line at the club?

Jones, Martial, Matic, Eric Bailly, Dean Henderson, and Axel Tuanzebe are just a few who could leave.

The manager, Arnold and the Glazers must make clear-headed football decisions about all of the above, but the reality is that some will stay because no top club can sanction the departures of as many as 10 players in a summer window and expect to replace them all. United must find a way to get rid of the dead wood, but retain the players who could be useful, because consistency is not something that can be expected next season. Getting rid of every player who doesn't measure up isn't as simple as balancing it.

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Mark thinks that the forward will stay at Man United.

The Ronaldo dilemma

After 12 years at Real Madrid, where he won two LaLiga titles, and two European Championships, the Portuguese forward signed a two-year contract with United last summer. He has scored 15 goals for United this season, but he has only scored one goal in eight games in the future and is starting to look like a passenger in the team.

United will look for a new centre-forward after Cavani leaves. It seems highly unlikely that whoever the new manager is,Ronaldo will be a regular starter with the likes of Rashford, Sancho and young Anthony Elanga all pushing to play, as well as whoever United sign up front.

What do United do with the player? He would be a useful member of the squad if he were to stay and accept a role as an impact substitute next season. An unhappyRonaldo would become an unwanted distraction. Even though it won't be cheap to pay up the final year of his contract, recent performances suggest that one of the world's greatest-ever players is.

If United are sensible, they would allow the new manager to start with a clean slate and not have to worry about how to deal with the superstars in the team.

Rangnick's role

After his stint as interim manager comes to an end this season, he will become a consultant at Old United. It's not clear what that actually means, with United already employing John Murtough as head of football operations and a former player as technical director.

If he is asked to join the football department at United, it will strengthen their ability to find the best emerging players but also give them access to the knowledge of a man who has helped build successful structures at Hoffenheim. Without a clear role, the German could confuse matters behind the scenes, which is why he needs a defined role.

If United decide to appoint Luis Enrique, they will have to wait until the end of his contract with Spain at the World Cup in 2022, which could extend his interim stint into next season. Regardless of his future role, United must make sure everyone knows what it involves before he starts.

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