Gregory's Two Girls backdrop
COMEDY . 1999 . 1h 56m . 4.6/10

Gregory's Two Girls_

"He's back - and he's got some serious explaining to do."

Twenty years after his teenage crush on a football-mad schoolgirl, Gregory is back at his old school, teaching English. When two of his pupils uncover evil practices at a local factory they want their teacher to help them expose the wrong-doer, who happens to be Greg's old schoolfriend.

Starring John Gordon Sinclair, Dougray Scott, Maria Doyle Kennedy
4.6/10
Rating
1h 56m
Runtime
1999
Year
Updated Feb 16, 2026
Gregory's Two Girls poster
He's back - and he's got some serious explaining to do.

Twenty years after his teenage crush on a football-mad schoolgirl, Gregory is back at his old school, teaching English. When two of his pupils uncover evil practices at a local factory they want their teacher to help them expose the wrong-doer, who happens to be Greg's old schoolfriend.

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Cast
John Gordon Sinclair stars as Gregory Underwood in Gregory's Two Girls.
John Gordon Sinclair →
Year context
Gregory's Two Girls was released 27 years ago in 1999.
Overview
Twenty years after his teenage crush on a football-mad schoolgirl, Gregory is back at his old school, teaching English. When two of his pupils uncover evil p...
Gregory's Two Girls is a Comedy film with a runtime of 1h 56m.

CAST (20)

John Gordon Sinclair
John Gordon Sinclair
Gregory Underwood
Dougray Scott
Dougray Scott
Fraser Rowan
Maria Doyle Kennedy
Maria Doyle Kennedy
Bel
Kevin Anderson
Kevin Anderson
Jon
Martin Schwab
Martin Schwab
Dimitri
Fiona Bell
Fiona Bell
Maddy Underwood
CM
Carly McKinnon
Frances
HM
Hugh McCue
Douglas
John Murtagh
John Murtagh
Headmaster
Alexander Morton
Alexander Morton
Teacher (Norman)
WH
William Harkness
Courier
AC
Albert Coulson
Bus Driver
Paul Birchard
Paul Birchard
American Executive
SH
Simon Huh
Asian Executive
Dawn Steele
Dawn Steele
Jan
CC
Constanzo Cacace
Italian Restauranteur
Gary Lewis
Gary Lewis
Mr. McCance
Anne Kidd
Anne Kidd
Headmaster's Secretary
Matt Costello
Matt Costello
Detective Gorrie
JS
Jane Stabler
Detective Ritchie

DETAILS

Release
Status
Released
Runtime
116 min (1h 56m)
Rating
4.6/10 (18 votes)

FREQUENTLY ASKED QUESTIONS

What is Gregory's Two Girls about?
Twenty years after his teenage crush on a football-mad schoolgirl, Gregory is back at his old school, teaching English. When two of his pupils uncover evil practices at a local factory they want their teacher to help them expose the wrong-doer, who happens to be Greg's old schoolfriend.
How long is Gregory's Two Girls?
Gregory's Two Girls has a runtime of 116 minutes (1h 56m).
Who stars in Gregory's Two Girls?
The cast of Gregory's Two Girls includes John Gordon Sinclair, Dougray Scott, Maria Doyle Kennedy, Kevin Anderson, Martin Schwab.
What is the rating of Gregory's Two Girls?
Gregory's Two Girls has a rating of 4.6 out of 10 based on 18 votes on TMDB.

GENRES (1)

Comedy
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