Under Ashley, the Magpies have always been knocked out of the competition by February, and have been humbled by lower-league opposition five times.
As United prepare for another third-round tie this weekend, here's a look at the Magpies' sorry record in the FA Cup since Mike Ashley took control:
2008
Third Round - Stoke City 0-0 Newcastle / Newcastle 4-1 Stoke City
Fourth Round - Arsenal 3-0 Newcastle
The Magpies were given a scare by the Championship side in Sam Allardyce's final game in charge, before recording a comfortable victory in the replay on the day Kevin Keegan returned as manager.
Goals from Michael Owen, Cacapa, James Milner and Damien Duff were enough to book a place in the fourth round, but United were then knocked out at the Emirates Stadium.
The visitors made a promising start showing good attacking intent. However, Emmanuel Adebayor struck shortly after the break and doubled the lead in the closing stages. Nicky Butt's late own-goal rounded off a miserable afternoon in the capital.
2009
Third Round - Hull City 0-0 Newcastle / Newcastle 0-1 Hull City
The Magpies earned a replay after a goalless draw at one of their relegation rivals.
But at home, a strong United line-up was knocked out of the competition by a second-string Hull outfit. Daniel Cousin scored the only goal of the game to book a fourth-round tie with Millwall.
Joe Kinnear described the defeat as a "smash and grab" by the visitors, and boos rang out at St James' Park as United's season went from bad to worse.
2010
Third Round - Plymouth Argyle 0-0 Newcastle / Newcastle 3-0 Plymouth Argyle
Fourth Round - West Brom 4-2 Newcastle
Hughton rang the changes for the Magpies trip to fellow Championship side Plymouth, and Fabrice Pancrate came closest to breaking the deadlock when he hit the post.
The replay was a comfortable affair with a Peter hat-trick extending United's unbeaten run to 13 matches.
But having been drawn against promotion rivals West Brom, Hughton made changes once again while Roberto Di Matteo named an unchanged lineup.
A volley from Andy Carroll gave the visitors hope after goals from Jonas Olsson and a Graham Dorrans' penalty. This was quickly extinguished when Ryan Taylor was dismissed for a foul on Jerome Thomas in the box. Dorrans scored his second spot-kick and Thomas' late goal made sure of the victory.
2011
Third Round - Stevenage 3-1 Newcastle
Surely a contender for one of the lowest moments of Mike Ashley's time in charge on Tyneside?
The Magpies were well-beaten by their League Two opponents who avenged their fourth-round defeat to the Magpies in 1998.
Stacy Long's deflected effort gave the hosts the lead, and Michael Bostwick long-range strike doubled their advantage.
Cheick Tiote was dismissed before Joey Barton pulled one back with an effort from distance in injury time. But there was still time for Peter Winn to restore Stevenage's two-goal cushion.
2012
Third Round - Newcastle 2-1 Blackburn Rovers
Fourth Round - Brighton 1-0 Newcastle
United managed to come from behind to progress to the fourth round courtesy of Jonas Gutierrez's injury-time winner.
David Goodwillie had fired Rovers in front, but Alan Pardew's side were drawn level courtesy of a majestic solo effort from Hatem Ben Arfa.
But for the second season in a row, the Magpies were dumped out of the competition by lower-league opposition.
Will Buckley grabbed the winner for the Seagulls in the 76th minute, with his effort looping in via a deflection off Mike Williamson.
2013
Third Round - Brighton 2-0 Newcastle
The Seagulls repeated the trick a season later as United fell to a seventh defeat in eight games.
Andrea Orlandi fired the hosts in front, and the visitors' chances of mounting a comeback were dealt a blow when Shola Ameobi was sent off for a second bookable offence.
Will Hoskins added a second late on to confirm another early exit for United.
2014
Third Round - Newcastle 1-2 Cardiff City
For the fourth season in a row under Pardew, United bowed out of the FA Cup at the hands of lower-league opposition.
Papiss Cisse had given the hosts the lead on the hour mark, capitalising on a rebound after Moussa Sissoko's effort.
But new Bluebirds boss Ole Gunnar Solskjaer introduced Fraizer Campbell and Craig Noone in the second half, and both forwards netted to earn Cardiff's first win on Tyneside in 51 years.
2015
Third Round - Leicester City 1-0 Newcastle
Under interim boss John Carver, United were dumped out of the competition at the third-round stage again - this time by the Premier League's bottom side.
Both sides made seven changes from their previous outings, and Leonardo Ulloa headed the Foxes ahead in the first half.
Remy Cabella had a strike before that ruled out for offside, but the Magpies failed to draw themselves level in a match devoid of quality.
2016
Third Round - Watford 1-0 Newcastle
Steve McClaren was the man in charge for United's latest foray in the FA Cup, but it ended in the same result.
Troy Deeney scored the only game of the game at Vicarage Road, pouncing on Gini Wijnaldum's poor backpass to round Rob Elliot and tap the ball into an empty net.
It was the fourth successive 1-0 defeat for the Magpies in a season which produced the second relegation of the Ashley era.
2017
Third Round - Birmingham City 1-1 Newcastle / Newcastle 3-1 Birmingham City
Fourth Round - Oxford United 3-0 Newcastle
United managed to make it to the fourth round for the first time in five seasons, requiring a replay to dispatch Birmingham at St James' Park.
But the Magpies were yet again knocked out of the competition by lower-league opposition with an embarrassing defeat at the Kassam Stadium.
With an immediate return to the Premiership the main goal, Rafa Benitez made nine changes for the fourth-round clash.
Kane Hemmings put the hosts in front, and Aleksandar Mitrovic missed a glorious chance to equalise from the penalty spot. Curtis Nelson doubled the advantage before Toni Martinez sealed an emphatic victory as Oxford progressed to the fifth round for the first time in 23 years.
2018
Third Round - Newcastle 3-1 Luton Town
Fourth Round - Chelsea 3-0 Newcastle
Benitez was rewarded for picking a strong line-up as United scored three times in a devastating nine-minute spell in the first half against the League Two leaders.
Danny Hylton pulled one back for the Hatters who pressed hard to pull themselves level, but the Magpies eased through to the fourth round.
However, United bowed out at the next hurdle after being handed a tricky trip to Stamford Bridge.
A Michy Batshuayi first-half double put the Blues in control, and former Sunderland wing-back Marcos Alonso made sure of the result with a free-kick 18 minutes from time.
2019
Third Round - Newcastle 1-1 Blackburn Rovers / Blackburn Rovers 2-4 Newcastle (AET)
Fourth Round - Newcastle 0-2 Watford
The Magpies managed to knock Blackburn out of the competition for the second time in the Ashley era - but needed extra-time in the replay to best their Championship opponents.
A late penalty for Matt Ritchie earned the hosts a replay at Ewood Park, where they raced into a two-goal lead courtesy of strikes from Sean Longstaff and Cal Roberts.
Former Magpie Adam Armstrong pulled one back for Rovers who then drew level with Darragh Lenihan's header. Joselu fired United back in front in extra-time from a rebound before Ayoze Perez added a fourth to seal an action-packed tie.
But Benitez's side were once again knocked out in the fourth round following a turgid tie at St James' Park. Andre Gray and Isaac Success scored as Watford eased past the Magpies en route to the FA Cup final.