Bucs fans have seen their team in this unique position time and time again since their team last won a major trophy in 2014, which was the Nedbank Cup under Serbian coach Vladimir Vermezovic.
Since then Pirates have reached the final of Nedbank Cup twice and they were defeated by the same team, SuperSport United on both occasions.
Coaches such as Eric Tinkler, Turkish coach Muhsin Ertuğral, Augusto Palacios and Kjell Jonevret have been brought in since Vermezovic's depature in 2014, but have all failed to deliver a major trophy.
The Bucs management then rehired Milutin 'Micho' Sredojevic, who was tasked with stabilizing the Bucs ship and laying the foundation for success prior to the start of the 2017/18 campaign.
Micho managed to revive Pirates and he turned the team into serious Premier Soccer League (PSL) title contenders, and they finished the season as runners-up behind a well-oiled Mamelodi Sundowns side.
This raised the hopes of the Bucs supporters coming into the current campaign and it has brought more pressure on the Serbian tactician, who won league titles and cup trophies in Sudan, Uganda and Ethiopia.
The Pirates squad were then reinforced with the signing of quality players such as Brilliant Khuzwayo, Ben Motshwari and Vincent Pule during the winter transfer window.
Defender Motshwari and forward Pule, who won trophies with Bidvest Wits, have already proved their quality having played an important role in helping Bucs reach the final and assert the team as one of the favourites to win this season's PSL title.
Khuzwayo was a serial winner with Kaizer Chiefs between 2012 and 2015, but the goalkeeper has been unlucky with injuries since arriving at Bucs. His quality is unquestioned and he is expected to make Pirates' number one spot his own once he is match fit.
With raised hopes and a formidable squad brings more pressure, and Sredojevic will obviously view the Telkom Knockout trophy as the perfect opportunity to clinch his maiden trophy in South Africa and ease the expectations on himself.
If he fails to deliver against a Baroka FC side which will be making its maiden appearance in a major cup final then the 2016 Caf Coach of the Year nominee will find himself in a dire situation like some of his predecessors.
Added pressure after failure to win in cup finals has eventually led to Bucs parting ways with coaches such as Roger De Sa and Tinkler in recent times, and Micho cannot afford to let the final chance slip.