Daniel Levy is known as a difficult negotiator.
The Tottenham chairman squeezed every penny out of United when the Red Devils turned to Dimitar Berbatov in 2008.
United also reportedly pulled out of the running for Luka Modric, who joined Real Madrid in 2012, as they did not want to haggle with Levy.
However, United could be ready to lock horns with Levy over Harry Kane's signature.
TOP STORY – WOODWARD READY TO BATTLE LEVY FOR KANE
Manchester United and Ed Woodward are ready to battle for the signing of Tottenham star Harry Kane, according to the Evening Standard.
Kane is reportedly considering his future at Tottenham and the England international striker is believed to be open to a switch to United at the end of the season.
United are yet to permanently replace Romelu Lukaku and Red Devils executive vice-chairman Woodward reportedly wants to lock horns with Spurs chairman Daniel Levy.
- Could United beat Borussia Dortmund to Jude Bellingham? Birmingham City's 16-year-old sensation Bellingham visited United's training ground on Monday and reportedly spoke to former manager Alex Ferguson as the Red Devils ramp up their interest. Bellingham is valued at around £30million.
- David Beckham's Inter Miami want to sign Manchester City star David Silva, reports The Mirror. Silva, out of contract at the end of the season, has been linked to fellow MLS franchise New York City – who are the sister club of Manchester City and part of the City Football Group.
- Tuttosport claims Juventus are targeting Valencia attacker Ferran Torres. The 20-year-old has also been linked to LaLiga champions Barcelona, Real Madrid and Premier League leaders Liverpool.
- United are prepared to pay £70m for Aston Villa captain Jack Grealish, says The Mirror. Grealish has emerged as one of United's prime transfer targets and the Red Devils are ready to test Villa's resolve as the Premier League strugglers face relegation.
- Paris Saint-Germain continue to target Napoli defender Kalidou Koulibaly. PSG have identified Koulibaly as Thiago Silva's replacement but Calciomercato says it will be difficult for the Ligue 1 holders to lower Napoli's demands. Koulibaly – also linked to the likes of United, Madrid, Tottenham and Manchester City – reportedly has a €150m termination clause.
- Kicker says Bundesliga champions Bayern Munich are considering signing on-loan Inter winger Ivan Perisic at season's end.