Cigar Mile Betting Guide

Aqueduct Racetrack hosts the Grade 1 Cigar Mile annually in late November, and the 2021 renewal will once again be a huge betting race for gamblers. Below, we will examine all the details for the race this year, as well as run through the recent winners of the competitive handicap.

Cigar Mile Event Details


The Cigar Mile is run annually at Aqueduct Racetrack and takes place in late November. It is a Grade 1 race, which takes place over a distance of one mile on a dirt surface. Horses aged three and older can enter the race, while there is a purse of $500,000 up for grabs for connections.

Cigar Mile Preview


The Cigar Mile Handicap will not be taking place until the end of 2021, which means that the entries for the competitive Grade 1 will not be made until nearer the time. However, we can assess the previous winners of the race to help find the winner of the race in 2021.


  • True Timber (2020)

  • Maximum Security (2019)

  • Patternrecognition (2018)

  • Sharp Azteca (2017)

  • Connect (2016)

  • Tonalist (2015)


The winner of the Cigar Mile last year was True Timber for trainer Jack Sisterson. He was the oldest winner of the race since 2013 and was the first six-year-old to win the race. The age of the recent winners could be a big indicator to help find a winner in the 2021 renewal. Horses aged three and four have had the best records in this race over recent years.


Maximum Security and Connect were both three when they won this race, while Tonalist and Sharp Azteca were aged four.


Jockey Javier Castellano has an excellent recent record in this race, as he has ridden the winner on two occasions in the past five years. His first win came with Connect in 2016, before he achieved back-to-back wins the following year, as he guided Sharp Azteca to glory in the Cigar Mile.


The route that the horse takes to the Cigar Mile could also be important background information. True Timber didn’t make his season debut until July in the year that he won the Cigar Mile. His first start came in an allowance race at Keeneland, where he was beaten by C Z Rocket. He later lined up over distances ranging between six and seven furlongs, which included runs in the Grade 2 Vosburgh Stakes and Lafayette Stakes.


Maximum Security took a very different route to the most recent winner, as his season started on the route to the Kentucky Derby. He made three starts before lining up for the opening Triple Crown race of the season, where he finished in 17th. However, he went into the Cigar Mile after back-to-back graded wins in the Grade 1 Haskell Invitational Stakes and the Grade 3 Bold Ruler Handicap.

Cigar Mile Event Information


The Cigar Mile was introduced in 1988 and was named in honor of Hall of Famer, Cigar, who won the race in 1994. It was renamed in honor of the horse three years after his victory. It has taken place every year, with the only exception coming in 1993 when the race was canceled.


Discreet Cat is the holder of the speed record in the Cigar Mile, as he finished the 2006 renewal in a time of 1:32.46. Congaree is the only horse to have won this race on more than one occasion, as he won in back-to-back years in 2002 and 2003. Jerry Bailey is the most successful jockey in the history of this race, with his fifth and final win coming with Congaree in 2003.


No trainer has achieved more wins in the Cigar Mile than Todd Pletcher, who recorded his fourth win in 2012 with Stay Thirsty. The most successful owners in the history of the Cigar Mile are Michael B. Tabor and Stonerside Stable, who have both owned the winner on two occasions.

Cigar Mile Betting Information


The Cigar Mile is a hugely popular betting race that takes place at Aqueduct. There are a number of different betting markets available to gamblers that will be looking to place a wager on the action. You can learn about some of the most popular markets below.


  • Win: The win market is the most popular market to make a bet on the Cigar Mile. Bets must be placed on the horse that crosses the line first to get returns.

  • Place: Place betting is also popular when it comes to making a wager on the Cigar Mile. Selections must be placed on a horse that will finish in the first two positions.

  • Exacta: Selections can also be made on the correct finishing order. Bets on this market must correctly predict the horses that finish in first and second in the Cigar Mile.

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