The affable Australian has watched his good friend, trainer Daniel Meagher, lead in his stable star on more than one occasion and wondered what could have been if not for the presence of the dominating Lim's Kosciuszko in many of Singapore's feature races.
A Group 1 Lion City Cup (1200m) and Group 1 Singapore Gold Cup (2000m) were two trophies that alluded Fitzsimmons last year, with Golden Monkey and Dream Alliance the runners-up respectively to the reigning Horse of the Year.
Then there was another Group 1 near-miss earlier, when Relentless ran second to Lim's Kosciuszko in the 2022 Singapore Derby (1800m) by a head. One could forgive Fitzsimmons, the 2022 Singapore champion trainer, for thinking 'what could have been'.
As it stands, Fitzsimmons has one Group 1 victory to his name, which was the 2023 Singapore Derby won by Golden Monkey. Supporters would think the five-year-old son of Star Turn will be his best bet to make it two in the $1 million Group 1 Kranji Mile (1600m) on Saturday.
Besides Golden Monkey , Fitzsimmons will field two other runners, Dream Alliance and Raising Sixty-One, in the 10-horse field, but the in-form runner would be Golden Monkey. After he drew the widest alley in gate 10, a usual cold ride would be the order of the day.
"He's been set for this race," said Fitzsimmons.
"The outside gate is not ideal, but at the same time, we were always going back with him anyway.
"He jumped too well the other day (in the Group 2 EW Barker Trophy over 1400m on 21 April), landed a bit closer and over-did it a little bit. We knew he doesn't have that run of foot when he's ridden closer.
"So the idea this weekend would be to ride him similar to when he won the (Singapore) Derby; just come straight out the back and put him to sleep.
"There doesn't appear to be a lot of speed in the race, which is unfortunate. But hopefully, a few other jockeys see that as an opportunity to ride their horses a bit closer.
"I'm really happy with him (Golden Monkey) and it's good to have (visiting jockey) Chad (Schofield) back up riding him."
While punters will most probably make Golden Monkey the second favourite to the obvious favourite Lim's Kosciusko, Fitzsimmons was not putting all his eggs in one basket.
"I'm happy with my three," he continued.
"Not much has gone right for Dream Alliance (x Into Mischief) since that Gold Cup run (last November).
"He was given no chance at his last start (in a Class 2 race over 1600m on 30 March); three-wide with no cover the whole race.
"He's the sort of horse that needs to switch off early and get cover, then use his turn of foot. Similar to Golden Monkey; he needs to be ridden quiet.
"But he has a beautiful barrier (five) and I'm sure he's going to appreciate having one of the best jockeys in the world (visiting jockey Mark Zahra) riding him this week. That's exciting."
Fitzsimmons would also appreciate some good old-fashioned luck for Raising Sixty-One , who will be ridden by jockey Bruno Queiroz.
"I love this horse," enthused Fitzsimmons of the five-year-old son of Belardo.
"But same as Dream Alliance ; not much has gone right for him.
"He was four-wide with no cover in the Gold Cup and ran fourth. He was three-wide no cover the whole race the other day (in a Class 2 race over 1600m on 4 May) and Cavalry got the camp on his back.
"He had a lighter weight (52.5kgs) but taking the earmuffs off him at his last start seemed to sharpen him up over the mile as I think he's a 2000m plus sort of horse.
"But with a good barrier (three), he could surprise a few. He's very tough, very honest and just keeps improving."
Like most successful trainers, Fitzsimmons is competitive to a fault but also realistic enough to know things will need to go his way to find a chink in Lim's Kosciuszko's armour.
"I'm hoping for speed in the race. Otherwise, it's hard to get close to 'Kosi'," he explained.
"It's tough to get past him anyway. Dan's (Meagher) done an incredible job to keep him going.
"But you never know in racing. Stranger things have happened, so we'll be out there doing our best."
