Marcelo Bielsa's side have suffered successive defeats, putting the Yorkshire giants under pressure to improve at the home of the Dutch champions.
With Manchester United to come on the opening day of the season, Bielsa knows that his Leeds squad can ill-afford to be off the pace when they take on last season's runners-up at Old Trafford.
However, while the Argentine will not pay too much attention to results at this stage of the summer, defeats against Fleetwood Town and Real Betis are far from ideal.
Leeds largely fielded a second-string side against Fleetwood, but there were members of the squad at Highbury that would have been hoping to impress.
Nevertheless, Leeds sides of varying quality have now conceded eight times in four games, putting the onus on delivering an improved defensive performance in the Netherlands.
Ajax are further through their pre-season campaign, with Erik ten Hag's squad having already played six times since the beginning of July.
Draws have recently been registered against each of Bayern Munich and RB Leipzig, results which arguably make the Eredivisie title winners the favourites to prevail in this contest.
Like his opposite number, performance over result will matter more to Ten Hag, but taking the scalp of a Premier League club would not go unnoticed ahead of the new season.
This game is being played three days before Ajax take on PSV Eindhoven in the Johan Cruyff Shield.
The upcoming meeting with PSV will almost certainly result in Ten Hag making mass substitutions during Wednesday's contest.
Jamie Shackleton may be given an opportunity alongside the Poland international, with Phillips unlikely to be risked after his busy summer with England.
Ajax possible starting lineup:
Stekelenburg; Mazraoui, Timber, Martinez, Tagliafico; Gravenberch, Blind, Klaassen; Berghuis, Haller, Tadic
Leeds United possible starting lineup:
Meslier; Dallas, Ayling, Koch, Firpo; Shackleton, Klich; Harrison, Rodrigo, Raphinha; Bamford
We say: Ajax 1-1 Leeds United
With the new season less than two weeks away, Bielsa will have inevitably upped the intensity in training.
While his players may benefit on the training pitch, it could hinder their efforts on Wednesday, leading us to predict a low-scoring draw.