Former Leeds and Newcastle midfielder Lee Bowyer oversaw a 3-2 victory against Barbados in his first game in charge of Montserrat.
Bowyer accepted the role with the CONCACAF side in early September, meaning he was in position in time for their Nations League B campaign opener on Saturday.
Lyle Taylor - who Bowyer worked with during his time at Charlton - found the top corner with his free-kick in the eighth minute of second-half added time to secure all three points.
It was Taylor's second of the game after he gave them the lead with just six minutes played, although Barbados found themselves ahead at the break.
An absolute rocket from Lyle Taylor 🇲🇸 in the dying minutes of the match! 🤩#CNL pic.twitter.com/zeB9GdPECf
— Concacaf Nations League (@CNationsLeague) September 9, 2023
Shane Codrington's own goal put the Emerald Boys level in the late stages of normal time, before Taylor stepped up to win it in the final moments.
Montserrat marks Bowyer's third job in management after guiding the Addicks to promotion from Sky Bet League One in 2019. He then accepted the role with Birmingham less than two years later.
Bowyer replaced Matt Lockwood in the position, with the Montserrat FA making no official announcement on the change to their coaching set-up.
Lockwood - who enjoyed lengthy spells with Dundee and Leyton Orient during his playing career - took charge of just two games in March.
Taylor reunited with Bowyer
The appointment sees goalscorer Taylor reunited with his previous promotion-winning manager.
The striker netted 22 goals and contributed a further 13 assists in 44 games across Charlton's successful 2018/19 campaign, and he was quick to heap praise on Bowyer at the time.
"He's a great man, honestly he's a great man," Taylor told Sporting Life at Wembley following their play-off final victory.
Charlton striker Lyle Taylor was near speechless after that game and who can blame him.
— Tom Carnduff (@TomCarnduff) May 26, 2019
Also full of praise for Lee Bowyer. “He’s a great man, honestly he’s a great man”#CAFC @CAFCofficial pic.twitter.com/fm3lsnVOiN
"It's been a pleasure. I said to him 'thank you' and he said to me 'no, thank you for choosing this club'.
"I chose the club because of him. So, it's a full circle, he wanted me, he thanked me for choosing here and I chose here because of him.
"We've done it together."
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