Chiefs have not known silverware since May 2015 when Stuart Baxter led them to the league title.
Since then, they have reached cup finals and come within minutes of lifting the league title, but it has all come to nothing with coaches changing from Steve Komphela, Giovanni Solinas, Ernst Middendorp, Gavin Hunt, and Baxter again.
The baton has now been handed to Arthur Zwane for this season
AmaKhosi start their latest trophy chase on Sunday afternoon away at Stellenbosch in the MTN8 quarterfinals in a game that will carry further weight for the club.
Facts state that inclusive of the latest league campaign, which is already underway, the MTN8 is now trophy number 30 that Chiefs are involved in through their silverware chase.
They have lost more points than they have gained in the league, and so taking aim at a four-game knockout tournament like the MTN8 provides a realistic trophy target.
Chiefs last won the MTN8 in 2014 and remain the most successful club in the competition with 15 titles.
From the day they lifted the league seven years ago, they have found no joy in 28 editions of the six competitions that they have been involved in.
Not only have Chiefs failed to lift the league in the last seven years they have also come short in all the domestic competitions – MTN8 (six times), Telkom KnockOut (five times), and Nedbank Cup (seven times).
Through this period, they have also been in the CAF Champions League twice and were also knocked out in the Confederations Cup play-off round in the 2018/19 season.
What worsens the pain for Chiefs is that Sundowns have since overtaken them as the most successful club in the PSL era years moving to 24 titles while AmaKhosi remain stuck on 20.
The Brazilians have won 14 trophies since Chiefs last went up a podium as champions.