On Wednesday, Boston will have the opportunity to extend its winning streak to 15 games, which would tie the franchise record set 80 years ago by Hall-of-Famer Ted Williams and the 1946 Red Sox.
With Tuesday night’s game moved to Wednesday afternoon due to inclement weather, the Sox will have a doubleheader at Fenway, offering a unique opportunity for them to not only tie but also set that long-standing record in the same day.
Check out our expert predictions and picks for the first game of the Red Sox-Orioles doubleheader on Wednesday, including Dimers’ best bets, live Kalshi odds, and more.
Red Sox vs. Orioles Betting Preview:
Here are the primary details for the first game of Wednesday’s doubleheader at Fenway Park:
| Game Detail | Information |
|---|---|
| Matchup | Baltimore Orioles at Boston Red Sox |
| Date | Wednesday, July 22, 2026 |
| Game | First game of a doubleheader |
| First Pitch | 1:35 p.m. ET |
| Venue | Fenway Park, Boston, Massachusetts |
| Orioles Probable Starter | Dean Kremer |
| Red Sox Probable Starter | Jake Bennett |
Kremer enters the matchup with a 1-2 record and 4.15 ERA, while Bennett is listed at 5-3 with a 2.35 ERA.
Kalshi Prices: Red Sox vs. Orioles
Kalshi’s pricing makes Boston the favorite but leaves the matchup relatively competitive.
The prediction platform also leans toward Baltimore staying within one run and toward the game finishing below the listed total.
| Market | Kalshi Selection | Current Price |
|---|---|---|
| Moneyline | Boston to win | 55¢ |
| Moneyline | Baltimore to win | 45¢ |
| Run Line | Boston wins by more than 1.5 runs | 38¢ |
| Run Line | Boston does not win by more than 1.5 runs | 63¢ |
| Total Runs | Over 9.5 | 47¢ |
| Total Runs | Under 9.5 | 54¢ |
Note: Kalshi prices can change throughout the day as traders submit new orders and respond to pitching updates, lineup announcements and more.
Dimers Win Probabilities: Red Sox vs. Orioles
Dimers’ simulation model gives Boston a slightly stronger chance of winning than the current Kalshi market does.
| Team | Dimers Win Probability | Kalshi Probability |
|---|---|---|
| Boston Red Sox | 58.3% | 55% |
| Baltimore Orioles | 41.7% | 45% |
After simulating the matchup 10,000 times, Dimers projects Boston to win 58.3% of the time. Baltimore wins the remaining 41.7% of simulations.
That creates a modest difference between the model and the market, as Dimers is 3.3 percentage points more bullish on Boston than Kalshi.
The expected pitching matchup may be part of that Boston lean as Bennett carries a substantially lower listed ERA than Kremer entering Wednesday night’s game.
Dimers Best Trade: Red Sox vs. Orioles
Dimers identifies Over 9.5 runs as the strongest projected value for the first game of Wednesday’s doubleheader.
The model gives the over a 53.2% probability and calculates a +6.2 percentage point advantage.
That is the clearest discrepancy between Dimers and Kalshi, where Over 9.5 is trading at only 47¢.
| Dimers Pick | Projected Probability | Model Edge (Percentage Points) | Best Available Odds |
|---|---|---|---|
| Over 9.5 runs | 53.2% | +6.2 | +110 |
| Red Sox to win | 58.3% | +3.3 | -127 |
| Red Sox -1.5 | 40.3% | +2.3 | +155 |
Kalshi and Dimers Comparison Recap: Red Sox vs. Orioles
Kalshi and Dimers agree that Boston should be favored in the first game of Wednesday’s doubleheader, but neither source treats the Red Sox as an overwhelming favorite.
Kalshi prices Boston at 55¢, while Dimers gives the Red Sox a 58.3% chance to win. That gap supports a fairly significant Boston moneyline edge.
Another meaningful difference is found in the total. Kalshi traders currently favor Under 9.5, pricing the over at 47¢ and the under at 54¢. Dimers takes the opposite position, projecting a 53.2% probability that the teams combine for at least 10 runs.
Prediction Markets for Red Sox vs. Orioles
Local Red Sox and Orioles fans in both Massachusetts and Maryland can now use prediction markets to trade on the MLB as an alternative to typical betting. Here are our top options, and available promo codes for new users:
| Platform | MLB Eligible? | July ’26 Sign-Up Bonus | Verified Promo Codes |
|---|---|---|---|
| Polymarket | Yes | $50 | CUSE , MASS , OREGON , SILIVE , CLEVE |
| Kalshi | Yes | $10 | SYRACUSE , OREGONLIVE1 , MASSLIVE1 , SILIVE , CLEVELAND |
| Novig | Yes | $50 | SYRACUSE , OREGON , MASSLIVE , CLEVELAND |
MLB Wednesday: Red Sox vs. Orioles
We emphasize that all of the MLB best trades and MLB predictions in this preview are based on 10,000 data-driven simulations of the Red Sox vs. Orioles, and they are correct at the time of publishing.
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