| 101. | OOTP 22 Ep 74: Oct '27 -- Four teams, Three Games, and One Wild Card Spot Left: Pittsburgh Pirates | 3 | Show |
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| 102. | OOTP 22 Ep 41: Dodgers Challenge: WORLD SERIES BOUND after Clutch Double from Austin Hays | 3 | Show |
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| 103. | OOTP 22 Ep 32: Dodgers Challenge: Vidal Brujan knocks in three runs in NLDS Game 1 Victory. | 3 | Show |
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| 104. | OOTP 22 Ep 33: 2024 Season Turnaround Begins: Pittsburgh Pirates | 3 | Show |
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| 105. | OOTP 22 Ep 74: Dodgers Challenge: 2024 Season Simulation | 3 | Show |
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| 106. | OOTP 22 Ep 51: Dodgers Challenge: We trade for Shane Bieber | 3 | Show |
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| 107. | OOTP 22 Ep 28: Dodgers Challenge: We trade for Aaron Nola | 3 | Show |
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| 108. | OOTP 22 Ep 34: Dodgers Challenge: SWEEP! NLDS SWEEP! Braves Swept in Second Straight Shutout | 3 | Show |
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| 109. | OOTP 22 Ep 56: Kumar Rocker is Dealing: Pittsburgh Pirates | 3 | Show |
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| 110. | OOTP 22 Ep 69 (Nice): Speed Sim to July 2027: Pittsburgh Pirates | 3 | Show |
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| 111. | OOTP 22 Ep 46: Dodgers Challenge: WORLD SERIES GAME 5 -- We meet again, Lucas Giolito | 3 | Show |
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| 112. | OOTP 22 Ep 55: Dodgers Challenge: The NL West Knife Fight Intensifies between Padres, Dodgers | 3 | Show |
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| 113. | OOTP 22 Ep 27: Dodgers Challenge: 8-game July win streak to extends NL West lead. | 3 | Show |
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| 114. | OOTP 22 Ep 37: Dodgers Challenge: EPIC COMEBACK Falls Short in NLDS Game 3 | 3 | Show |
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| 115. | OOTP 22 Ep 19: Dodgers Challenge: Mountcastle and Arozarena HRs Lead LA to Undefeated Start. | 3 | Show |
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| 116. | OOTP 22 Ep 24: Dodgers Challenge: Pache, Kelenic Rake in Win Against Padres | 3 | Show |
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| 117. | OOTP 22 Ep 53: 2025 NLDS Game 4 vs. St. Louis Cardinals: Pittsburgh Pirates | 3 | Show |
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| 118. | OOTP 22 Ep 89: Reds blow out the Pirates: Pittsburgh Pirates | 2 | Show |
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| 119. | OOTP 22 Ep 60: Back in the 2026 NL Central Race: Pittsburgh Pirates | 2 | Show |
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| 120. | OOTP 22 Ep 20: Dodgers Challenge: Extra Innings Needed for Third Time Against Diamondbacks | 2 | Show |
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| 121. | OOTP 22 Ep 66: Dodgers Challenge: NLCS GAME 5 2023 -- On the Wrong End in Extra Innings | 2 | Show | Extra Innings
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| 122. | OOTP 22 Ep 95: PITTSBURGH PIRATES SERIES FINALE: PART TWO: Simulating to the 2040s | 2 | Show |
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| 123. | OOTP 22 Ep 57: Dodgers Challenge: 2023 NLDS GAME 1 -- Shane Bieber Dominates on Mound, at Plate | 2 | Show |
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| 124. | OOTP 22 Ep 94: PITTSBURGH PIRATES SERIES FINALE: PART ONE | 2 | Show |
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| 125. | OOTP 22 Ep 61: Dodgers Challenge: 2023 NLDS GAME 5 -- LA Shows Yu No Mercy | 2 | Show |
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| 126. | OOTP 22 Ep 43: Dodgers Challenge: WORLD SERIES GAME 2 -- We Need Extra Innings to Reach an Outcome | 2 | Show | Extra Innings
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| 127. | OOTP 21 -- Episode 3 -- Rule 5 Draft -- Pittsburgh Pirates | 2 | |
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| 128. | OOTP 21 -- Episode 61 -- Quiet Bats lead to 2025 NLDS Game 2 Loss -- Pittsburgh Pirates | 2 | |
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| 129. | OOTP 22 Ep 25: Dodgers Challenge: Cristian Pache wins Hitter of Month in May 2022 | 2 | Show |
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| 130. | OOTP 22 Ep 67: 2027 Opening Day and Season Preview: Pittsburgh Pirates | 2 | Show |
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| 131. | OOTP 22 Ep 57: Buccos get crushed 15-4 by the Cardinals: Pittsburgh Pirates | 2 | Show |
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| 132. | OOTP 21 -- Episode 12 -- Good Eye Evan White! -- Pittsburgh Pirates | 2 | |
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| 133. | OOTP 22 Ep 88: Great American Ballpark Sucks: Pittsburgh Pirates | 2 | Let's Play |
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| 134. | OOTP 22 Ep 71 Pt 1: The Greatest World Series Comeback of All-Time | 2 | Show |
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| 135. | OOTP 22 Ep 55: 2026 Offseason Recap and Spring Training Preview: Pittsburgh Pirates | 2 | Show |
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| 136. | OOTP 22 Ep 67: Dodgers Challenge: NLCS GAME 6 2023 -- Cruising to the National League Pennant | 2 | Show |
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| 137. | OOTP 22 Ep 54: Dodgers Challenge: LA, San Diego separate from rest of MLB | 2 | Show |
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| 138. | OOTP 22 Ep 36: 2025 Opening Day Dejection: Pittsburgh Pirates | 2 | Show |
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| 139. | OOTP 22 Ep 75: I despise the St. Louis Cardinals: Pittsburgh Pirates | 2 | Show |
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| 140. | OOTP 21 -- Episode 29 -- Bucs earn a commanding NL Central lead -- Pittsburgh Pirates | 2 | |
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| 141. | OOTP 22 Ep 68: Dodgers Challenge: LA scores 20 runs to start 2023 World Series against Blue Jays | 2 | Show |
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| 142. | OOTP 22 Ep 76: 2028 Spring Training Preview -- Our Final Ride?: Pittsburgh Pirates | 2 | Show |
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| 143. | OOTP 22 Ep 69 (Nice): Dodgers Challenge: Another Easy World Series Victory | 2 | Show |
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| 144. | OOTP 22 Ep 59: Dodgers Challenge: 2023 NLDS GAME 3 -- The Revenge of Cody Bellinger | 2 | Show |
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| 145. | OOTP 22 Ep 71 Pt 2: The Greatest World Series Comeback of All-Time: Part 2 | 2 | Show |
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| 146. | OOTP 22 Ep 52: Dodgers Challenge: Surge Lands LA atop NL West | 2 | |
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| 147. | OOTP 22 Ep 58: Dodgers Challenge: 2023 NLDS GAME 2 -- PITCHERS DUEL FOR THE AGES | 2 | Show |
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| 148. | OOTP 22 Ep 60: Dodgers Challenge: 2023 NLDS GAME 4 -- Cristian Pache Extends Series with Clutch Hit | 2 | Show |
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| 149. | OOTP 22 Ep 68: An Icky Month of April 2027: Pittsburgh Pirates | 2 | Show |
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| 150. | OOTP 22 Ep 82: Battling Injuries through Turbulent May: Pittsburgh Pirates | 2 | Show |
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| 151. | OOTP 22 Ep 64: Dodgers Challenge: NLCS GAME 3 2023 -- Andres Gimenez, Ryan Mountcastle go deep | 2 | Show |
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| 152. | OOTP 22 Ep 50: Dodgers Challenge: Cristian Pache Can't be Stopped through May 2023 | 2 | Show |
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| 153. | OOTP 22 Ep 62: Three Picks in the First 33 Selections of the 2026 MLB Draft: Pittsburgh Pirates | 2 | Show |
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| 154. | OOTP 22 Ep 65: Dodgers Challenge: NLCS GAME 4 2023 -- Pivotal Contest goes Back-and-Forth | 2 | Show |
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| 155. | OOTP 22 Ep 75: Dodgers Challenge: Andres Gimenez's Walk-off, Wild-Card Winning Home Run | 1 | Show |
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| 156. | OOTP 22 Ep 85: New-Look Buccos Pummel Reds in First Inning: Pittsburgh Pirates | 1 | Show |
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| 157. | OOTP 21 -- Episode 35 -- Game 2 of the 2022 NLDS -- Pittsburgh Pirates | 1 | |
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| 158. | OOTP 22 Ep 64: Teams start dropping like flies in the NL Central Race: Pittsburgh Pirates | 1 | Show |
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| 159. | OOTP 21 -- Episode 15 -- Cubs can't hold off a late-inning rally -- Pittsburgh Pirates | 1 | |
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| 160. | OOTP 22 Ep 76: Dodgers Challenge: 2024 NLDS Game 1 @ San Diego Padres | 1 | Show |
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| 161. | OOTP 22 Ep 66: 2026 Season Wrap-Up and Award Voting: Pittsburgh Pirates | 1 | Show |
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| 162. | OOTP 21 -- Episode 27 -- Rule 4 June Draft -- Pittsburgh Pirates | 1 | |
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| 163. | OOTP 22 Ep 58: The Mediocre Month of April in 2026: Pittsburgh Pirates | 1 | Show |
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| 164. | OOTP 22 Ep 70: The 2027 MLB Draft: Pittsburgh Pirates | 1 | Show |
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| 165. | OOTP 22 Ep 62: Dodgers Challenge: NLCS GAME 1 2023 -- Vidal Brujan's lead off Home Run Sets Tone | 1 | Show |
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| 166. | OOTP 21 -- Episode 4 -- 2021 Opening Day -- Pittsburgh Pirates | 1 | |
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| 167. | OOTP 22 Ep 29: Dodgers Challenge: Jarred Kelenic rakes during "tough" August | 1 | Show |
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| 168. | OOTP 22 Ep 86: Dodgers Challenge: 2024 World Series Game 1 vs. Cleveland Indians | 1 | Show |
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| 169. | OOTP 22 Ep 72: March toward the Wild Card Begins: Pittsburgh Pirates | 1 | Show |
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| 170. | OOTP 22 Ep 80: Dodgers Challenge: 2024 NLDS Game 5 @ San Diego Padres | 1 | Show |
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| 171. | OOTP 21 -- Episode 21 -- 2021 Late Season Push -- Pittsburgh Pirates | 1 | |
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| 172. | OOTP 21 -- Episode 8 -- Let's Draft! 2021 Rule 4 Draft -- Pittsburgh Pirates | 1 | |
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| 173. | OOTP 22 Ep 59: 2026 is going off the Rails: Pittsburgh Pirates | 1 | Show |
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| 174. | OOTP 22 Ep 91: Dodgers Challenge: 2024-2025 Offseason Extravaganza | 1 | Show |
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| 175. | OOTP 22 Ep 78: Undefeated through Two Games: Pittsburgh Pirates | 1 | Show |
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| 176. | OOTP 22 Ep 95: Dodgers Challenge: 2025 Wild Card Game vs. Milwaukee Brewers | 1 | Show |
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| 177. | OOTP 22 Ep 91: Simulating to the 2028 All-Star Break: Pittsburgh Pirates | 1 | Show |
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| 178. | OOTP 22 Ep 80: Cardinals Ruin our Perfect Start in 2028: Pittsburgh Pirates | 1 | Show |
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| 179. | OOTP 21 -- Episode 46 -- In-depth Minor League Review -- Pittsburgh Pirates | 1 | Review |
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| 180. | OOTP 22 Ep 73: Dodgers Challenge: Offseason Extravaganza -- Signing Giolito to 1yr/$100M contract | 1 | Show |
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| 181. | OOTP 21 -- Episode 11 -- The Alec Bohm Show -- Pittsburgh Pirates | 1 | Show |
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| 182. | OOTP 21 -- Episode 42 -- Pirates Pummel Yankees -- Pittsburgh Pirates | 1 | |
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| 183. | OOTP 22 Ep 79: 2028 Game Three -- A Defensive Gem: Pittsburgh Pirates | 1 | Show |
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| 184. | OOTP 22 Ep 61: 2026 All-Star Voting and Pre-ASG Simulating: Pittsburgh Pirates | 1 | Show |
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| 185. | OOTP 21 -- Episode 7 -- The Time I Met Bryce Harper in Real Life -- Pittsburgh Pirates | 1 | |
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| 186. | OOTP 22 Ep 90: Pirates Late-Inning Rally Falls Short: Pittsburgh Pirates | 1 | Show |
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| 187. | OOTP 22 Ep 94: Dodgers Challenge: Simulating through Season End 2025 | 1 | Show |
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| 188. | OOTP 22 Ep 73: September 2027 is a bloodbath for the second Wild Card: Pittsburgh Pirates | 1 | Show |
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| 189. | OOTP 21 -- Episode 22 -- Can the Bucs really win the Division twice in a row? -- Pittsburgh Pirates | 1 | | The Division
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| 190. | OOTP 21 -- Episode 41 -- 2023 MLB Draft -- Pittsburgh Pirates | 1 | |
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| 191. | OOTP 22 Ep 65: Strong End to 2026 Season Despite Missing Playoffs: Pittsburgh Pirates | 1 | Show |
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| 192. | OOTP 21 -- Episode 48 -- Pirates vs. Orioles July 2023 -- Pittsburgh Pirates | 1 | |
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| 193. | OOTP 22 Ep 93: Dodgers Challenge: Simulating through May 2025 | 1 | Show |
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| 194. | OOTP 21 -- Episode 47 -- Bullpen, Right Field address at Deadline -- Pittsburgh Pirates | 1 | Let's Play |
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| 195. | OOTP 21 -- Episode 26 -- Raking and Dealing -- Pittsburgh Pirates | 1 | |
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| 196. | OOTP 22 Ep 81: 2028 Buccos in the NL Central Driver's Seat through April: Pittsburgh Pirates | 1 | Show |
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| 197. | OOTP 21 -- Episode 33 -- Pirates clinch 2022 NL Central -- Pittsburgh Pirates | 1 | |
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| 198. | OOTP 22 Ep 63: Dodgers Challenge: NLCS GAME 2 2023 -- Bieber goes seven, but offense sputters. | 1 | Show |
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| 199. | OOTP 21 -- Episode 44 -- The Cardinals strike back -- Pittsburgh Pirates | 1 | |
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| 200. | OOTP 21 -- Episode 43 -- Brady Singer throws a Complete Game -- Pittsburgh Pirates | 1 | |
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