Winless so far in the King's Cup in Thailand in 2004 and 2018, the Soca Warriors could not rewrite that script in this year's edition of the tournament at the 700th Anniversary Chiang Mai Stadium, on Thursday when they went down 2-1 to Tajikistan in their opening match.
They will have another opportunity to change that though when they take the field on Sunday against the host nation, who also went under to Malaysia 2-1 on penalties, in the other match of the evening's double-header after the teams finished 1-1 at the end of regulation time.
But with the Warriors, boosted by the return of instrumental midfielder Kevin Molino, who had been away due to injury, took the field intending to change the results of the past.
Coach Angus Eve thought they should have had the opener in the 16th minute when the speedy Levi Garcia used his pace to telling effect, taking the ball byline on the right side before he centred for the unmarked Noah Powder.
But with the goal at his mercy, Powder's attempt ricochetted off defender Vakhdat Khanonov before going to safety.
Tajikistan came close to taking the lead eight minutes later, but Tajikistan's Shahron Samiev could not reach Mukhammadzhon Rakimov's left-side centre before the onrushing Frenderup in time. However, the T&T custodian received a blow to the neck after a collision with Samiev.
The opener came in the 27th minute. Garcia who had been in the centre of the action would head Frenderup's long kick-out into the path of his brother Judah Garcia to slot the ball past the advancing Rustam Yatimov in the Tajikistan goal.
The goal gave the Warriors a 1-0 advantage at the halfway stage but the Tajikistanis intensified their search for the equaliser in the moments that followed, and they got it.
A detrimental blunder by defender Sheldon Bateau allowed Rakimov to gallop on to a through-ball before he placed it under the legs of Frenderup for a 1-1 scoreline in the 47th minute.
Some eight minutes later, Frenderup had to be substituted as he came down hard after tipping Samiev's directed header on goal overbar. He was replaced by backup goalkeeper Marvin Phillip.
In the fluctuating affair, both teams were prevented by the acrobatics of the respective goalkeepers, until Tajikistan got the winner in the 75th minute. Shervoni Mabatshoev, given room to run with the ball, drew three defenders on top of the area before slipping it to the unmarked Ekhson Pandzhshanbe to connect with a low shot that beat substitute goalkeeper Phillip in the T&T goal.
The result left Eve fuming from a game he felt, they should have won.
"I am extremely disappointed in the result tonight (yesterday morning in T&T), I thought we did enough without taking our chances. I believe we shouldn't have lost the game tonight and I am very disappointed with the players' lack of professionalism in the second half."
"We have to review the tapes of this match to see where we made mistakes. In international football, if you don't take your chances and you make mistakes in the back, then you will lose the game, and that is what happened to us today, hence why I said I was disappointed in the lack of professionalism because I felt we had enough goalscoring opportunities in the first half to lose," Eve said.
Meanwhile, Frenderup will be assessed by the medical staff on Friday, according to a release on Thursday, but is expected to be available for selection in Sunday's match.