After finishing second in a similar event at the same track thirteen days later he was stepped up in class and took third place in the Listed Queen's Vase over two miles at Royal Ascot.

In 2018 Twilight Payment ran second to Order of St George in the Saval Beg Stakes and then finished third behind Flag of Honour in the Curragh Cup.

On 27 July he started favourite for Her Majesty's Plate over fourteen furlongs on Good to Firm ground at Down Royal and recorded his first victory in 20 months as he won "comfortably" by three and a half lengths from Law of Spin after taking the lead approaching the last quarter mile.

In November the gelding was consigned to the Goffs Horses In Training sale and was bought for €200,000 by the bloodstock agents Kerr & Co Ltd.[8] In the early part of 2019 Twilight Payment raced in the colours of Jackie Bolger, his trainer's wife.

He began the season in April when he finished second in a minor event at Gowran Park and then ran fourth to Master of Reality in the Vintage Crop Stakes at Navan.

[9] The gelding followed up in the Curragh Cup over the same distance on 28 June, leading from the start and fighting off the sustained challenge of the 2018 Irish Derby winner Latrobe to prevail by a neck.

"[11] Twilight Payment was then acquired by the Australian businessman Lloyd Williams and transferred to the stable of Joseph Patrick O'Brien at Owning Hill, County Kilkenny.

Twilight Payment began his next campaign with a trip to Saudi Arabia where he finished seventh behind Call The Wind in the Longines Turf Handicap at Riyadh on 29 February.

Ridden by Wayne Lordan he led from the start and drew away in the final furlong to win by two and a half lengths from Barbados, with Sovereign, Falcon Eight and Master of Reality finishing behind.

[12] On 18 July he repeated his 2019 success in the Curragh Cup, starting odds on favourite and winning "easily" by eight lengths from Master of Reality after taking the lead three furlongs from the finish.