All Episodes

Shoulda Bet More with Will Hill - Ep. 389 Dave Ross

Shoulda Bet More with Will Hill - Ep. 388 Geoff Schwartz

Shoulda Bet More with Will Hill - Ep. 387 Dustin Swedelson

Shoulda Bet More with Will Hill - Ep. 386 Jensen Lewis

Shoulda Bet More with Will Hill - Ep. 385 Jeff Parles

Shoulda Bet More with Will Hill - Ep. 384 Jonathan Von Tobel

Shoulda Bet More with Will Hill - Ep. 383 Kiev O'neil

Shoulda Bet More with Will Hill - Ep. 383 Brad Thomas

Shoulda Bet More with Will Hill - Ep. 382 Stormy Buonantony

Shoulda Bet More with Will Hill - Ep. 381 Dave Ross

Shoulda Bet More with Will Hill - Ep. 380 Chris Fallica

Shoulda Bet More with Will Hill - Ep. 379 Gill Alexander

Shoulda Bet More with Will Hill - Ep. 378 Jensen Lewis

Shoulda Bet More with Will Hill - Ep. 377 Brett Ciancia

Shoulda Bet More with Will Hill - Ep. 376 Mike Sando

Shoulda Bet More with Will Hill - Ep. 375 Jeff Parles

Shoulda Bet More with Will Hill - Ep. 374 John Jastremski

Shoulda Bet More with Will Hill - Ep. 373 Brad Powers

Shoulda Bet More with Will Hill - Ep. 372 Mitch Moss

Shoulda Bet More with Will Hill - Ep. 371 Kiev O'Neil

Shoulda Bet More with Will Hill - Ep. 370 Steve Fezzik

Shoulda Bet More with Will Hill - Ep. 369 Jonathan Von Tobel

Shoulda Bet More with Will Hill - Ep. 360 Chris Fallica

Shoulda Bet More with Will Hill - Ep. 359 Mitch Moss

Shoulda Bet More with Will Hill - Ep. 358 Jeff Parles

Shoulda Bet More with Will Hill - Ep. 356 Steve Phillips

Shoulda Bet More with Will Hill - Ep. 355 Luke Swain

Shoulda Bet More with Will Hill - Ep. 354 Gill Alexander

Shoulda Bet More with Will Hill - Ep. 352 Geoff Schwartz

Shoulda Bet More with Will Hill - Ep. 351 Chris Fallica

Shoulda Bet More with Will Hill - Ep. 350 Jensen Lewis

Shoulda Bet More with Will Hill - Ep. 349 Kelley Bydlon

Shoulda Bet More with Will Hill - Ep. 348 Jeff Parles

Shoulda Bet More with Will Hill - Ep. 347 Jonathan Von Tobel

Shoulda Bet More with Will Hill - Ep. 346 Chris Macero

Shoulda Bet More with Will Hill - Ep. 345 Kiev O'Neil

Shoulda Bet More with Will Hill - Ep. 344 Gill Alexander

Shoulda Bet More with Will Hill - Ep. 343 Jensen Lewis

Shoulda Bet More with Will Hill - Ep. 342 Doug Kezirian

Shoulda Bet More with Will Hill - Ep. 341

Shoulda Bet More with Will Hill - Ep. 340 Jonathan Von Tobel

Shoulda Bet More with Will Hill - Ep. 339 Chris Fallica

Shoulda Bet More with Will Hill - Ep. 338 Steve Fezzik

Shoulda Bet More with Will Hill - Ep. 337 Dave Ross

Shoulda Bet More with Will Hill - Ep. 336 Gill Alexander

Shoulda Bet More with Will Hill - Ep. 335 Mitch Moss

Shoulda Bet More with Will Hill - Ep. 334 Sammy P

Shoulda Bet More with Will Hill - Ep. 333 Jonathan Von Tobel

Shoulda Bet More with Will Hill - Ep. 332 Chris Macero

Shoulda Bet More with Will Hill - Ep. 331 Chris Fallica

Shoulda Bet More with Will Hill - Ep. 330 Doug Kezirian

Shoulda Bet More with Will Hill - Ep. 329

Shoulda Bet More with Will Hill - Ep. 328 Jeff Parles

Shoulda Bet More with Will Hill - Ep. 327 Geoff Schwartz

Shoulda Bet More with Will Hill - Ep. 326 Jonathan Von Tobel

Shoulda Bet More with Will Hill - Ep. 325 Kelley Bydlon

Shoulda Bet More with Will Hill - Ep. 324 Gill Alexander

Shoulda Bet More with Will Hill - Ep. 323 Dave Ross

Shoulda Bet More with Will Hill - Ep. 322 Chris Fallica

Shoulda Bet More with Will Hill - Ep. 321 Matt Youmans

Shoulda Bet More with Will Hill - Ep. 320 Steve Fezzik

Shoulda Bet More with Will Hill - Ep. 319 Ian Eagle

Shoulda Bet More with Will Hill - Ep. 318 Jonathan Von Tobel

Shoulda Bet More with Will Hill - Ep. 317 Jeff Parles

Shoulda Bet More with Will Hill - Ep. 317 Mitch Moss

Shoulda Bet More with Will Hill - Ep. 316 Gill Alexander

Shoulda Bet More with Will Hill - Ep. 315 John Laghezza

Shoulda Bet More with Will Hill - Ep. 314 Kiev O’Neil

Shoulda Bet More with Will Hill - Ep. 313 Tim Murray

Shoulda Bet More with Will Hill - Ep. 312 Chris Fallica

Shoulda Bet More with Will Hill - Ep. 311 Jeff Parles

Shoulda Bet More with Will Hill - Ep. 310 Jonathan Von Tobel

Shoulda Bet More with Will Hill - Ep. 309

Shoulda Bet More with Will Hill - Ep. 308 Kiev O’Neil

Shoulda Bet More with Will Hill - Ep. 307 Jensen Lewis

Shoulda Bet More with Will Hill - Ep. 306 Chris Fallica

Shoulda Bet More with Will Hill - Ep. 305 Adam Burke

Shoulda Bet More with Will Hill - Ep. 304 Brad Thomas

Shoulda Bet More with Will Hill - Ep. 303 Todd Wishnev

Shoulda Bet More with Will Hill - Ep. 302 Ryan Glasspiegel

Shoulda Bet More with Will Hill - Ep. 301 Dave Ross

Shoulda Bet More with Will Hill - Ep. 300 Gill Alexander

Shoulda Bet More with Will Hill - Ep. 299 Jeff Parles

Shoulda Bet More with Will Hill - Ep. 298 Kelley Bydlon

Shoulda Bet More with Will Hill - Ep. 297 Colby Marchio

Shoulda Bet More with Will Hill - Ep. 296 Kiev O'Neil

Shoulda Bet More with Will Hill - Ep. 295 Jensen Lewis

Shoulda Bet More with Will Hill - Ep. 294 Jonathan Von Tobel

Shoulda Bet More with Will Hill - Ep. 293 John Jastremski

Shoulda Bet More with Will Hill - Ep. 292 Julian Edlow

Shoulda Bet More with Will Hill - Ep. 291

Shoulda Bet More with Will Hill - Ep. 290 Mitch Moss

Shoulda Bet More with Will Hill - Ep. 289 Dave Ross

Shoulda Bet More with Will Hill - Ep. 288 Gill Alexander

Shoulda Bet More with Will Hill - Ep. 287 Sam Panayotovich

Shoulda Bet More with Will Hill - Ep. 286 Chris "The Bear" Fallica

Shoulda Bet More with Jonathan Von Tobel - Ep. 285

Shoulda Bet More with Will Hill - Ep. 284

Shoulda Bet More with Will Hill - Ep. 283 Kiev O'Neil

Shoulda Bet More with Will Hill - Ep. 282 Jeff Parles

Shoulda Bet More with Will Hill - Ep. 281

Shoulda Bet More with Will Hill - Ep. 280 Jensen Lewis

Shoulda Bet More with Will Hill - Ep. 279 Geoff Schwartz

Shoulda Bet More with Will Hill - Ep. 278 Brad Powers

Shoulda Bet More with Will Hill - Ep. 277 Dave Ross

Shoulda Bet More with Will Hill - Ep. 276 Gill Alexander

Shoulda Bet More with Will Hill - Ep. 275 Jeff Parles

Shoulda Bet More with Will Hill - Ep. 274 Tim Murray

Shoulda Bet More with Will Hill - Ep. 273 Chris Fallica

Shoulda Bet More with Will Hill - Ep. 272 Jonathan Von Tobel

Shoulda Bet More with Will Hill - Ep. 271 Mike Sando

Shoulda Bet More with Will Hill - Ep. 270 Jeff Parles

Shoulda Bet More with Will Hill - Ep. 269 Brad Powers

Shoulda Bet More with Will Hill - Ep. 268 Brad Thomas

Shoulda Bet More with Will Hill - Ep. 267 Kiev O’Neil

Shoulda Bet More with Will Hill - Ep. 266 Kelley Bydlon

Shoulda Bet More with Will Hill - Ep. 265 Jeff Parles

Shoulda Bet More with Will Hill - Ep. 264 Geoff Schwartz

Shoulda Bet More with Will Hill - Ep. 263 Jonathan Von Tobel

Shoulda Bet More with Will Hill - Ep. 262 Chris "The Bear" Fallica

Shoulda Bet More with Will Hill - Ep. 261 Gill Alexander

Shoulda Bet More with Will Hill - Ep. 260 Mitch Moss

Shoulda Bet More with Will Hill - Ep. 259 Tim Murray

Shoulda Bet More with Will Hill - Ep. 258 Dave Ross

Shoulda Bet More with Will Hill - Ep. 257 Jensen Lewis

Shoulda Bet More with Will Hill - Ep. 256 Jeff Parles

Shoulda Bet More with Will Hill - Ep. 255

Shoulda Bet More with Will Hill - Ep. 254 Tommy Lorenzo

Shoulda Bet More with Will Hill - Ep. 253 Chris "The Bear" Fallica

Shoulda Bet More with Will Hill - Ep. 252 Kiev O'neil

Shoulda Bet More with Will Hill - Ep. 251 Jonathan Von Tobel

Shoulda Bet More with Will Hill - Ep. 250 Iain MacMillan

Shoulda Bet More with Will Hill - Ep. 249 Geoff Schwartz

Shoulda Bet More with Will Hill - Ep. 248 Matt Youmans

Shoulda Bet More with Will Hill - Ep. 247

Shoulda Bet More with Will Hill - Ep. 246 Gill Alexander

Shoulda Bet More with Will Hill - Ep. 245 Ben Wilson

Shoulda Bet More with Will Hill - Ep. 244 Jeff Parles

Shoulda Bet More with Will Hill - Ep. 243 Nic Larson

Shoulda Bet More with Will Hill - Ep. 242 Brad Powers

Shoulda Bet More with Will Hill - Ep. 241 Dave Ross

Shoulda Bet More with Will Hill - Ep. 240 Jensen Lewis

Shoulda Bet More with Will Hill - Ep. 239 Adam Kaufman

Shoulda Bet More with Will Hill - Ep. 238 Sammy P

Shoulda Bet More with Will Hill - Ep. 237 - Stormy Buonantony

Shoulda Bet More with Will Hill - Ep. 236 - Jonathan Von Tobel

Shoulda Bet More with Will Hill - Ep. 235 - Chris “The Bear” Fallica

Shoulda Bet More with Will Hill - Ep. 234 - Geoff Schwartz

Shoulda Bet More with Will Hill - Ep. 233 - Mitch Moss

Shoulda Bet More with Will Hill - Ep. 232 - John Jastremski

Shoulda Bet More with Will Hill - Ep. 231 - Gill Alexander

Shoulda Bet More with Will Hill - Ep. 230 - Kiev O'Neil

Shoulda Bet More with Will Hill - Ep. 229 - "The Bear" Chris Fallica

Shoulda Bet More with Will Hill - Ep. 228 - Gill Alexander

Shoulda Bet More with Will Hill - Ep. 227

Shoulda Bet More with Will Hill - Ep. 226 - Drew Dinsick

Shoulda Bet More with Will Hill - Ep. 225 - Chris Macero

Shoulda Bet More with Will Hill - Ep. 224 - Jonathan Von Tobel

Shoulda Bet More with Will Hill - Ep. 223 - Jeff Parles

Shoulda Bet More with Will Hill - Ep. 222

Shoulda Bet More with Will Hill - Ep. 221 - Ben Wilson

Shoulda Bet More with Will Hill - Ep. 220 - Sammy P

Shoulda Bet More with Will Hill - Ep. 219 - Ricky G

Shoulda Bet More with Will Hill - Ep. 218 - Jonathan Von Tobel

Shoulda Bet More with Will Hill - Ep. 217 - Mitch Moss

Shoulda Bet More with Will Hill - Ep. 216 - Will Hill!

Shoulda Bet More with Will Hill - Ep. 215 - Matt Grissom

Shoulda Bet More with Will Hill - Ep. 214 - Kelley Bydlon

Shoulda Bet More with Will Hill - Ep. 213 - Gill Alexander

Shoulda Bet More with Will Hill - Ep. 212 - Brad Thomas

Shoulda Bet More with Will Hill - Ep. 211 - Dustin Swedelson

Shoulda Bet More with Will Hill - Ep. 210 - Jeff Parles

Shoulda Bet More with Will Hill - Ep. 209

Shoulda Bet More with Will Hill - Ep. 208 - Jonathan Von Tobel

Shoulda Bet More with Will Hill - Ep. 207 - Dave Ross

Shoulda Bet More with Will Hill - Ep. 206 - Adam Kaufman

Shoulda Bet More with Will Hill - Ep. 205 - John Jastremski

Shoulda Bet More with Will Hill - Ep. 204 - Kelley Bydlon

Shoulda Bet More with Will Hill - Ep. 203 - Mike Somich

Shoulda Bet More with Will Hill - Ep. 202 - NicLarson

Shoulda Bet More with Will Hill - Ep. 201 - Geoff Schwartz

Shoulda Bet More with Will Hill - Ep. 200 - Gill Alexander

Shoulda Bet More with Will Hill - Ep. 199 - Drew Dinsick

Shoulda Bet More with Will Hill - Ep. 198 - Raheem Palmer

Shoulda Bet More with Will Hill - Ep. 197 - Jeff Parles

Shoulda Bet More with Will Hill - Ep. 196 - Sammy P

Shoulda Bet More with Will Hill - Ep. 195 - Jonathan Von Tobel

Shoulda Bet More with Will Hill - Ep. 194 - Aaron Schatz

Shoulda Bet More with Will Hill - Ep. 193 - Kelley Bydlon

Shoulda Bet More with Will Hill - Ep. 192 - Matt Youmans

Shoulda Bet More with Will Hill - Ep. 191 - Kiev O'Neil

Shoulda Bet More with Will Hill - Ep. 190 - Todd Wishnev

Shoulda Bet More with Will Hill - Ep. 189 - "The Bear" Chris Fallica

Shoulda Bet More with Will Hill - Ep. 188 - Gill Alexander

Shoulda Bet More with Will Hill - Ep. 187 - NicLarson

Shoulda Bet More with Will Hill - Ep. 186 - Jonathan Von Tobel

Shoulda Bet More with Will Hill - Ep. 185 - Stuckey

Shoulda Bet More with Will Hill - Ep. 184 - Iain MacMillan

Shoulda Bet More with Will Hill - Ep. 183 - Jeff Parles

Shoulda Bet More with Will Hill - Ep. 182 - Ian Eagle

Shoulda Bet More with Will Hill - Ep. 181 - Reed Wallach

Shoulda Bet More with Will Hill - Ep. 180 - Dave Ross

Shoulda Bet More with Will Hill - Ep. 179 - John Laghezza

Shoulda Bet More with Will Hill - Ep. 178 - Reed Wallach

Shoulda Bet More with Will Hill - Ep. 177 - Kiev O'Neil

Shoulda Bet More with Will Hill - Ep. 176 - Jonathan Von Tobel

Shoulda Bet More with Will Hill - Ep. 175 - Mitch Moss

Shoulda Bet More with Will Hill - Ep. 174 - Jeff Parles

Shoulda Bet More with Will Hill - Ep. 173 - John Jastremski

Shoulda Bet More with Will Hill - Ep. 172 - Dustin Swedelson

Shoulda Bet More with Will Hill - Ep. 171 - Todd Wishnev

Shoulda Bet More with Will Hill - Ep. 170 - Brad Thomas

Shoulda Bet More with Will Hill - Ep. 169 - Geoff Schwartz

Shoulda Bet More with Will Hill - Ep. 168 - Gill Alexander

Shoulda Bet More with Will Hill - Ep. 167 - Sammy P

Shoulda Bet More with Will Hill - Ep. 166 - Kiev O'Neil

Shoulda Bet More with Will Hill - Ep. 165 - Jeff Parles

Shoulda Bet More with Will Hill - Ep. 164 - Jason Weingarten

Shoulda Bet More with Will Hill - Ep. 163 - Kelley Bydlon

Shoulda Bet More with Will Hill - Ep. 162 - Jonathan Von Tobel (JVT)

Shoulda Bet More with Will Hill - Ep. 161 - Dave Ross

Shoulda Bet More with Will Hill - Ep. 160 - Matt Youmans

Shoulda Bet More with Will Hill - Ep. 159 - Jeff Parles

Shoulda Bet More with Will Hill - Ep. 158 - John Jastremski

Shoulda Bet More with Will Hill - Ep. 134 - Iain MacMillan

Shoulda Bet More with Will Hill - Ep. 156 - Kiev O'Neil

Shoulda Bet More with Will Hill - Ep. 155 - Aaron Schatz

Shoulda Bet More with Will Hill - Ep. 154 - Brad Powers

Shoulda Bet More with Will Hill - Ep. 153 - Jonathan Von Tobel (JVT)

Shoulda Bet More with Will Hill - Ep. 152 - "The Bear" Chris Fallica

Shoulda Bet More with Will Hill - Ep. 151 - Thor Nystrom

Shoulda Bet More with Will Hill - Ep. 150 - Jeff Parles

Shoulda Bet More with Will Hill - Ep. 149 - Reed Wallach

Shoulda Bet More with Will Hill - Ep. 148 - Gill Alexander

Shoulda Bet More with Will Hill - Ep. 147 - Brad Powers

Shoulda Bet More with Will Hill - Ep. 146 - Mitch Moss

Shoulda Bet More with Will Hill - Ep. 145 - Dave Ross

Shoulda Bet More with Will Hill - Ep. 144 - Jonathan Von Tobel (JVT)

Shoulda Bet More with Will Hill - Ep. 143 - Jeff Parles

Shoulda Bet More with Will Hill - Ep. 142 - "The Bear" Chris Fallica

Shoulda Bet More with Will Hill - Ep. 141 - Mike Sando

Shoulda Bet More with Will Hill - Ep. 140 - Matt Youmans

Shoulda Bet More with Will Hill - Ep. 139 - Kiev O'Neil

Shoulda Bet More with Will Hill - Ep. 138 - Paul Howard

Shoulda Bet More with Will Hill - Ep. 137 - Adam Kaufman

Shoulda Bet More with Will Hill - Ep. 136 - Jeff Parles

Shoulda Bet More with Will Hill - Ep. 135 - John Jastremski

Shoulda Bet More with Will Hill - Ep. 134 - Iain MacMillan

Shoulda Bet More with Will Hill - Ep. 133 - Doug Kazirian

Shoulda Bet More with Will Hill - Ep. 132 - Matkafee

Shoulda Bet More with Will Hill - Ep. 131 - Brad Thomas

Shoulda Bet More with Will Hill - Ep. 130 - Gill Alexander

Shoulda Bet More with Will Hill - Ep. 129- Jonathan Von Tobel

Shoulda Bet More with Will Hill - Ep. 128 - "The Bear" Chris Fallica

Shoulda Bet More with Will Hill - Ep. 127 - Kiev O'Neil

Shoulda Bet More with Will Hill - Ep. 126 - Sammy P

Shoulda Bet More with Will Hill - Ep. 125 - Jeff Parles

Shoulda Bet More with Will Hill - Ep. 124 - Scott Seidenberg

Shoulda Bet More with Will Hill - Ep. 123 - Tommy Lorenzo

Shoulda Bet More with Will Hill - Ep. 122 - Chris Macero

Shoulda Bet More with Will Hill - Ep. 121 - Dave Ross

Shoulda Bet More with Will Hill - Ep. 120 - Matt Youmans

Shoulda Bet More with Will Hill - Ep. 119 - Reed Wallach

Shoulda Bet More with Will Hill - Ep. 118 - Jeff Parles

Shoulda Bet More with Will Hill - Ep. 117 - Brad Powers

Shoulda Bet More with Will Hill - Ep. 116 - Dave Ross

Shoulda Bet More with Will Hill - Ep. 115 - Gill Alexander

Shoulda Bet More with Will Hill - Ep. 114 - Mitch Moss

Shoulda Bet More with Will Hill - Ep. 113 - Jeff Parles

Shoulda Bet More with Will Hill - Ep. 112 - MLB Postseason Preview with NicLarson

Shoulda Bet More with Will Hill - Ep. 111 - Kiev O'Neil

Shoulda Bet More with Will Hill - Ep. 110 - Chris Macero

Shoulda Bet More with Will Hill - Ep. 109 - Stuckey

Shoulda Bet More with Will Hill - Ep. 108 - Scott Seidenberg

Shoulda Bet More with Will Hill - Ep. 107 - Femi Abebefe

Shoulda Bet More with Will Hill - Ep. 106 - Iain MacMillan

Shoulda Bet More with Will Hill - Ep. 105 - Doug Kazirian

Shoulda Bet More with Will Hill - Ep. 104 - Jeff Parles

Shoulda Bet More with Will Hill - Ep. 103 - Jason Weingarten

Shoulda Bet More with Will Hill - Ep. 102 - Matkafee

Shoulda Bet More with Will Hill - Ep. 101 - Adam Kaufman

Shoulda Bet More with Will Hill - Ep. 100 - Sammy P

Shoulda Bet More with Will Hill - Ep. 99 - FranchiseKF

Shoulda Bet More with Will Hill - Ep. 98 - Mike Sando

Shoulda Bet More with Will Hill - Ep. 97 - Joey Isaks

Shoulda Bet More with Will Hill - Ep. 96 - Ian Eagle

Shoulda Bet More with Will Hill - Ep. 95 - John Laghezza

Shoulda Bet More with Will Hill - Ep. 94 - "The Bear" Chris Fallica

Shoulda Bet More with Will Hill - Ep. 93 - Scott Seidenberg

Shoulda Bet More with Will Hill - Ep. 92 - Gill Alexander

Shoulda Bet More with Will Hill - Ep. 91 - Mitch Moss

Shoulda Bet More with Will Hill - Ep. 90 - Matt Youmans

Shoulda Bet More with Will Hill - Ep. 89 - Steve Fezzik

Shoulda Bet More with Will Hill - Ep. 88 - Jeff Parles

Shoulda Bet More with Will Hill - Ep. 87 - John Jastremski

Shoulda Bet More with Will Hill - Ep. 86 - Hitman

Shoulda Bet More with Will Hill - Ep. 85 - Brad Thomas

Shoulda Bet More with Will Hill - Ep. 84 - Aaron Schatz

Shoulda Bet More with Will Hill - Ep. 83 - Femi Abebefe

Shoulda Bet More with Will Hill - Ep. 82 - Geoff Schwartz

Shoulda Bet More with Will Hill - Ep. 81 - Adnan Virk

Shoulda Bet More with Will Hill - Ep. 80 - Dave Ross

Shoulda Bet More with Will Hill - Ep. 79 - Kiev O'Neil

Shoulda Bet More with Will Hill - Ep. 78 - Jonathan Von Tobel

Shoulda Bet More with Will Hill - Ep. 77 - Julian Edlow

Shoulda Bet More with Will Hill - Ep. 76 - "The Bear" Chris Fallica

Shoulda Bet More with Will Hill - Ep. 75 - Jeff Parles

Shoulda Bet More with Will Hill - Ep. 74 - Reed Wallach

Shoulda Bet More with Will Hill - Ep. 73 - Gill Alexander

Shoulda Bet More with Will Hill - Ep. 72 - Brad Powers

Shoulda Bet More with Will Hill - Ep. 71 - Drew Dinsick

Shoulda Bet More with Will Hill - Ep. 70 - Alex B. Smith

Shoulda Bet More with Will Hill - Ep. 69 - Adam Chernoff

Shoulda Bet More with Will Hill - Ep. 68 - Jason Weingarten

Shoulda Bet More with Will Hill - Ep. 67 - Scott Seidenberg

Shoulda Bet More with Will Hill - Ep. 66 - Matt Grissom

Shoulda Bet More with Will Hill - Ep. 65 - Ben Wilson

Shoulda Bet More with Will Hill - Ep. 64 - Jonathan Von Tobel

Shoulda Bet More with Will Hill - Ep. 63 - Kelley Bydlon

Shoulda Bet More with Will Hill - Ep. 62 - Jason McIntyre

Shoulda Bet More with Will Hill - Ep. 61 - Jeff Parles

Shoulda Bet More with Will Hill - Ep. 60 - Matt Grissom

Shoulda Bet More with Will Hill - Ep. 59 - Adam Kaufman

Shoulda Bet More with Will Hill - Ep. 58 - Dave Ross

Shoulda Bet More with Will Hill - Ep. 57 - Mitch Moss

Shoulda Bet More with Will Hill - Ep. 56 - Dustin Swedelson

Shoulda Bet More with Will Hill - Ep. 55 - Gill Alexander

Shoulda Bet More with Will Hill - Ep. 54 - Jonathan Von Tobel

Shoulda Bet More with Will Hill - Ep. 53 - Brad Thomas

Shoulda Bet More with Will Hill - Ep. 52 - Scott Seidenberg

Shoulda Bet More with Will Hill - Ep. 51 - Mike Sando

Shoulda Bet More with Will Hill - Ep. 50 - NicLarson

Shoulda Bet More with Will Hill - Ep. 49 - Andy McCollough

Shoulda Bet More with Will Hill - Ep. 48 - Drew Dinsick

Shoulda Bet More with Will Hill - Ep. 47 - Brandon Anderson

Shoulda Bet More with Will Hill - Ep. 46 - Raheem Palmer

Shoulda Bet More with Will Hill - Ep. 45 - Matkafee

Shoulda Bet More with Will Hill - Ep. 44 - Fred Segal (Freezing Cold Takes)

Shoulda Bet More with Will Hill - Ep. 43 - Kelley Bydlon

Shoulda Bet More with Will Hill - Ep. 42 - Aaron Schatz

Shoulda Bet More with Will Hill - Ep. 41 - Ryan Glasspiegel

Shoulda Bet More with Will Hill - Ep. 40 - Jason Weingarten

Shoulda Bet More with Will Hill - Ep. 39 - Matt Youmans

Shoulda Bet More with Will Hill - Ep. 38 - "The Bear" Chris Fallica

Shoulda Bet More with Will Hill - Ep. 37 - Iain MacMillan

Shoulda Bet More with Will Hill - Ep. 36 - Todd Wishnev

Shoulda Bet More with Will Hill - Ep. 35 - Jeff Parles

Shoulda Bet More with Will Hill - Ep. 34 - Stuckey

Shoulda Bet More with Will Hill - Ep. 33 - Mitch Moss

Shoulda Bet More with Will Hill - Ep. 32 - Jonathan Von Tobel

Shoulda Bet More with Will Hill - Ep. 31

Shoulda Bet More with Will Hill - Ep. 30 - Iain MacMillan

Shoulda Bet More with Will Hill - Ep. 29 - Kiev O'Neil

Shoulda Bet More with Will Hill - Ep. 28 - Steve Fezzik

Shoulda Bet More with Will Hill - Ep. 27 - Tim Kurkjian

Shoulda Bet More with Will Hill - Ep. 26 - Jeff Parles

Shoulda Bet More with Will Hill - Ep. 25 - Reed Wallach

Shoulda Bet More with Will Hill - Ep. 24 - Adnan Virk (Oscars Special)

Shoulda Bet More with Will Hill - Ep. 23 - "The Bear" Chris Fallica

Shoulda Bet More with Will Hill - Ep. 22 - Jason Weingarten

Shoulda Bet More with Will Hill - Ep. 21 - Jonathan Von Tobel

Shoulda Bet More with Will Hill - Ep. 20 - Ian Eagle

Shoulda Bet More with Will Hill - Ep. 19 - Todd Wishnev

Shoulda Bet More with Will Hill - Ep. 18 - Kelley Bydlon

Shoulda Bet More with Will Hill - Ep. 17 - Gill Alexander

Shoulda Bet More with Will Hill - Ep. 16 - Matt Hamilton

Shoulda Bet More with Will Hill - Ep. 15 - Jeff Parles

Shoulda Bet More with Will Hill - Ep. 14 - Kiev O'Neil

Shoulda Bet More with Will Hill - Ep. 13 - Julian Edlow

Shoulda Bet More with Will Hill - Ep. 12 - Drew Dinsick

Shoulda Bet More with Will Hill - Ep. 11 - Iain MacMillan

Shoulda Bet More with Will Hill - Ep. 10 - Stuckey

Shoulda Bet More with Will Hill - Ep. 9 - Jonathan Von Tobel

Shoulda Bet More with Will Hill - Ep. 8 - The Hitman

Shoulda Bet More with Will Hill - Ep. 7 - Steve Fezzik

Shoulda Bet More with Will Hill - Ep. 6 - Aaron Schatz

Shoulda Bet More with Will Hill - Ep. 5 - Chris Fallica

Shoulda Bet More with Will Hill - Ep. 4 - Mike Sando

Shoulda Bet More with Will Hill - Ep. 3 - 12/26

Shoulda Bet More with Will Hill - Ep. 2 - 12/22

Shoulda Bet More with Will Hill - Ep. 1 - 12/18