The 36-year-old failed to earn his side a share of the spoils as the Australian side lost 1-0 to Wellington Phoenix, who ended the game with nine men.
Advertisement
Le Fondre earned himself a reputation of being a fox in the box during his time in England where he scored 12 Premier League goals for the Royals in the 2012-13 season.
And he has starred since making the move Down Under in 2018 where he has won two league championships.
Advertisement
But he couldn't help his team against Wellington after missing two penalties at the death in Saturday's A-League clash.
Sydney were awarded a first penalty in the fifth minute of added time after Tim Payne was judged to have handled the ball.
Up stepped Le Fondre, but his powerful strike to the bottom right corner was well saved by Oliver Sail.
The ball was parried out back across, with Phoenix's Callan Elliot then penalised for a handball after stopping a cross back into the six-yard box.
Advertisement
Advertisement
It was take two for Le Fondre in the ninth minute of stoppage time, but this time he failed to hit the target after blazing his spot-kick over the bar.
He immediately slumped to the turf as Sail celebrated wildly with his teammates in what proved to be the last chance of the match.
Advertisement
The result leaves Sydney eighth in the table - two points behind Wellington in sixth.
Sydney now trail league leaders Melbourne City by 12 points.
Le Fondre has struggled for consistency this season for Sydney having scored just three goals in nine matches in all competitions.
Advertisement
Wellington boss Ufuk Talay praised his team's fighting spirit after they had Nicholas Pennington and Bozhidar Kraev shown red cards in the second half.
He said: "Do we want to play with nine men every game?
"No we don't but in this case we've had to deal with this situation and the boys came up trumps.
"I thought the boys showed fantastic character to get through that (drama) and we walked away with the three points."
Advertisement
CSKA Moscow 
FC Rostov 
Leicester 
Chelsea 
Valencia 
Betis 
Dynamo Kyiv 
Chornomorets Odesa 
Verona 
Inter 
Bayer Leverkusen 
FC Heidenheim 
Borussia Dortmund 
SC Freiburg 
VFL Wolfsburg 
Union Berlin 
Arsenal 
Nottingham Forest 
Everton 
Brentford 
Spartak Moscow 
Lokomotiv Moscow 
Rangers 
Dundee Utd 
Atletico Madrid 
Alaves 
Lens 
Marseille 
Ingulets Petrove 
Shakhtar Donetsk 
AC Milan 
Juventus 
ST Malo 
Bordeaux 
Manchester City 
Tottenham 
Eintracht Frankfurt 
Werder Bremen 
Girona 
Espanyol 
Feyenoord 
Heerenveen 
ST Etienne 
Montpellier 
Grenoble Foot 38 
Heart Of Midlothian 
Celtic 
Reims 
Lyon 
PSV 
Groningen 
Celta Vigo 
Barcelona 
Benfica 
Estrela Da Amadora 
Sparta Rotterdam 
AZ Alkmaar 
Southampton 
Liverpool